[ CAS No. 133625-87-3 ] {[proInfo.proName]}

Name: 133625-87-3|(S)-tert-Butyl 2,2-dimethyl-4-vinyloxazolidine-3-carboxylate|95%
Brand: Ambeed
SKU: A782016
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3d Animation Molecule Structure of 133625-87-3

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Quality Control of [ 133625-87-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 133625-87-3 ]

Product Details of [ 133625-87-3 ]

CAS No. :	133625-87-3	MDL No. :	MFCD09033561
Formula :	C₁₂H₂₁NO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SEDZCRLQHSPEFD-VIFPVBQESA-N
M.W :	227.30	Pubchem ID :	11020618
Synonyms :

Calculated chemistry of [ 133625-87-3 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.75
Num. rotatable bonds :	4
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	66.86
TPSA :	38.77 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.17 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.11
Log Po/w (XLOGP3) :	2.13
Log Po/w (WLOGP) :	2.16
Log Po/w (MLOGP) :	1.33
Log Po/w (SILICOS-IT) :	1.6
Consensus Log Po/w :	2.07

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.33
Solubility :	1.07 mg/ml ; 0.00471 mol/l
Class :	Soluble
Log S (Ali) :	-2.58
Solubility :	0.604 mg/ml ; 0.00266 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.67
Solubility :	4.83 mg/ml ; 0.0212 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.57

Safety of [ 133625-87-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 133625-87-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 133625-87-3 ]
Downstream synthetic route of [ 133625-87-3 ]

[ 133625-87-3 ] Synthesis Path-Upstream 1~2

1
[ 133625-87-3 ]
[ 91103-37-6 ]

Yield	Reaction Conditions	Operation in experiment
76%	With toluene-4-sulfonic acid In methanol at 0 - 20℃;	To a solution of tert-butyl (4S)-2,2-dimethyl-4-vinyl-1,3-oxazolidine-3-carboxylate (1.90 g, 8.36 mmol) in methanol (83 mL) was added p-toluenesulfonic acid monohydrate (0.80 g, 4.2 mmol) at 0° C. The mixture was slowly warmed to room temperature overnight. The reaction mixture was diluted with saturated NaHCO₃solution, concentrated, and then diluted with ethyl acetate. The organic layer was washed with sat. NaHCO₃(2×) and brine, dried over Na₂SO₄, filtered and concentrated to give the desired product as colorless oil (1.187 g, 76percent). ¹H NMR (400 MHz, CDCl₃) δ 5.81 (1H, m), 5.25 (2H, m), 4.90 (1H, m), 4.25 (1H, br s), 3.67 (2H, m), 1.45 (9H, s) ppm.
76%	With toluene-4-sulfonic acid In methanol at 0 - 20℃;	Step 2. tert-Butyl [(1S)-1-(hydroxymethyl)prop-2-en-1-ylJcarbamateTo a solution of tert-butyl (4S)-2,2-dimethyl-4-vinyl- 1,3 -oxazolidine-3 -carboxylate (1.90 g, 8.36 mmol) in methanol (83 mL) was addedp-toluenesulfonicacid monohydrate (0.80 g, 4.2 mmol) at 0 °C. The mixture was slowly warmed to room temperature overnight. The reaction mixture was diluted with saturated NaHCO3 solution, concentrated, and then diluted with ethyl acetate. The organic layer was washed with sat. NaHCO3 (2x) and brine, dried over Na2SO4, filtered andconcentrated to give the desired product as colorless oil (1.187 g, 76percent). ‘H NMR (400 MHz, CDC13) 5.81 (1H, m), 5.25 (2H, m), 4.90 (1H, m), 4.25 (1H, br s), 3.67 (2H, m), 1.45 (9H, s) ppm.
76%	With toluene-4-sulfonic acid In methanol at 0 - 20℃;	To a solution of tert-butyl (4S)-2,2-dimethyl-4-vinyl-l,3-oxazolidine-3- carboxylate (1.90 g, 8.36 mmol) in methanol (83 mL) was added /?-toluenesulfonic acid monohydrate (0.80 g, 4.2 mmol) at 0 °C. The mixture was slowly warmed to room temperature overnight. The reaction mixture was diluted with saturated NaHCCte solution, concentrated, and then diluted with ethyl acetate. The organic layer was washed with sat. NaHCC"3 (2x) and brine, dried over Na₂S04, filtered and concentrated to give the desired product as colorless oil (1.187 g, 76percent). NMR (400 MHz, CDCb) δ 5.81 (1H, m), 5.25 (2H, m), 4.90 (1H, m), 4.25 (1H, br s), 3.67 (2H, m), 1.45 (9H, s) ppm.

76%

With toluene-4-sulfonic acid In methanol; water at 0 - 20℃;

To a solution of tert-butyl(4S)-2,2-dimethyl-4-vinyl-1,3-oxazolidine-3-carboxylate (1.90 g, 8.36 mmol) in methanol (83 mL) was added p-toluenesulfonic acid monohydrate (0.80 g, 4.2 mmol) at 0° C. The mixture was slowly warmed to room temperature overnight. The reaction mixture was diluted with saturated NaHCO₃solution, concentrated, and then diluted with ethyl acetate. The organic layer was washed with sat. NaHCO₃(2×) and brine, dried over Na₂SO₄, filtered and concentrated to give the desired product as colorless oil (1.187 g, 76percent). ¹H NMR (400 MHz, CDCl₃) δ 5.81 (1H, m), 5.25 (2H, m), 4.90 (1H, m), 4.25 (1H, br s), 3.67 (2H, m), 1.45 (9H, s) ppm.

Reference： [1] Patent: US2014/121198, 2014, A1, . Location in patent: Paragraph 0645; 0647
[2] Patent: WO2015/26818, 2015, A1, . Location in patent: Page/Page column 44
[3] Patent: WO2015/157257, 2015, A1, . Location in patent: Page/Page column 37; 38
[4] Patent: US2015/361094, 2015, A1, . Location in patent: Paragraph 0354
[5] Tetrahedron Asymmetry, 2001, vol. 12, # 6, p. 817 - 819
[6] Organic Letters, 2005, vol. 7, # 5, p. 847 - 849
[7] European Journal of Organic Chemistry, 2006, # 19, p. 4440 - 4450
[8] Patent: WO2004/14893, 2004, A2, . Location in patent: Page 110; 111
[9] Patent: WO2016/42089, 2016, A1, . Location in patent: Page/Page column 171; 172

2
[ 133625-87-3 ]
[ 89985-86-4 ]

Reference： [1] Chemistry Letters, 1987, p. 2085 - 2088

[ 133625-87-3 ] Synthesis Path-Downstream 1~52

1
[ 75-11-6 ]
[ 95715-87-0 ]
[ 133625-87-3 ]

Yield	Reaction Conditions	Operation in experiment
75%	With trimethylaluminum; zinc In tetrahydrofuran for 12h; Ambient temperature;

Reference： [1]Moriwake, Toshio; Hamano, Shin-ichi; Saito, Seiki; Torii, Sigeru [Chemistry Letters, 1987, p. 2085 - 2088]

2
[ 133625-87-3 ]
[ 89985-86-4 ]

Reference： [1]Chemistry Letters,1987,p. 2085 - 2088

3
[ 197218-82-9 ]
[ 133625-87-3 ]

Yield	Reaction Conditions	Operation in experiment
69%	In various solvent(s) at 175 - 180℃; for 6h;

Reference： [1]Ravi Kumar, Jalluri S.; Datta, Apurba [Tetrahedron Letters, 1997, vol. 38, # 38, p. 6779 - 6780]

4
[ 1779-49-3 ]
[ 95715-87-0 ]
[ 133625-87-3 ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: Methyltriphenylphosphonium bromide With potassium hexamethylsilazane In tetrahydrofuran; toluene at 20℃; for 1h; Stage #2: (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine In tetrahydrofuran; toluene at 20℃; for 3.5h;
77%	Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.0833333h; Stage #2: (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine In tetrahydrofuran; hexane at 20℃; for 18h;	64-65.1 Step 1 : (S)-tert-butyl 2,2-dimethyl-4-vinyloxazolidine-3-carboxylate A suspension of MePPh3Br (Fluka, 8.57 g, 23.99 mmol) in THF (218 ml) was stirred and cooled to -78 °C. A solution of 2.5 M n-BuLi in hexanes (Sigma Aldrich, 10.47 ml, 26.2 mmol) was added dropwise over 5 min, and the reaction was slowly warmed to RT. (R)- (+)-3-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde (Sigma Aldrich; 5 g, 21.81 mmol) was added dropwise via syringe, and the resulting suspension was stirred at RT for 18 h. The reaction was carefully quenched with sat. aq. NH4C1 and extracted with Et20. The combined organics were dried over Na2S04, filtered, and concentrated in vacuo. DCM was added, and the crude reaction was adsorbed onto silica and chromatographically purified (eluent: 0 to 30% EtOAc/hexanes), giving the product, (S)-tert-butyl 2,2- dimethyl-4-vinyloxazolidine-3-carboxylate, as a colorless oil (3.8 g, 77%): FontWeight="Bold" FontSize="10" H NMR (MeOH-d4) δ: 5.75 - 5.89 (m, 1H), 5.10 - 5.25 (m, 2H), 4.32 (br. s., 1H), 4.03 - 4.12 (m, 1H), 3.73 (d, J = 8.4 Hz, 1H), 1.57 (s, 3H), 1.49 (s, 3H), 1.44 (s, 9H).
65%	With n-butyllithium In tetrahydrofuran at -78 - 20℃; for 21h;

64%	Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 1h; Stage #2: (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine In tetrahydrofuran; hexane at 20℃; for 12h;	19.1 tert-Butyl (4S)-2,2-dimethyl-4-vinyl-1,3-oxazolidine-3-carboxylate To a suspension of methyl triphenylphosphonium bromide (5.63 g, 15.8 mmol) in tetrahydrofuran (140 mL) was added 2.5 M n-butyllithium in hexane (7.35 mL, 18.4 mmol). The deep red solution was stirred at 0° C. for 1 h. Then a solution of tert-butyl (4R)-4-formyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (from Aldrich, 3.01 g, 13.1 mmol) in tetrahydrofuran (7.3 mL) was added drop wise at 0° C. The red solution was warmed to room temperature and stirred for 12 h. Hexanes was added to the reaction mixture in 4:1 (v/v) ratio. The suspension was filtered through Celite and the filtrate concentrated. The resultant residue was purified by flash chromatography (eluting with 10% ethyl acetate in hexanes) to give the desired compound as colorless oil (1.92 g, 64%).
64%	Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 1h; Stage #2: (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine In tetrahydrofuran; hexane at 0 - 20℃; for 12h;	J1.1 Step 1. tert-Butyl (4S)-2, 2-dimethyl-4-vinyl-1, 3-oxazolidine-3-carboxylate Step 1. tert-Butyl (4S)-2, 2-dimethyl-4-vinyl-1, 3-oxazolidine-3-carboxylateTo a suspension of methyl triphenylphosphonium bromide (5.63 g, 15.8mmol) in tetrahydrofuran (140 mL) was added 2.5 M n-butyllithium in hexane (7.35 mL, 18.4 mmol). The deep red solution was stirred at 0 °C for 1 h. Then a solution of tert-butyl (4R)-4-formyl-2,2-dimethyl- 1,3 -oxazolidine-3 -carboxylate (from Aldrich,3.01 g, 13.1 mmol) in tetrahydrofuran (7.3 mL) was added drop wise at 0 °C. The red solution was warmed to room temperature and stirred for 12 h. Hexanes was added to the reaction mixture in 4:1 (v/v) ratio. The suspension was filtered through Celite and the filtrate concentrated. The resultant residue was purified by flash chromatography5 (eluting with 10% ethyl acetate in hexanes) to give the desired compound as colorless oil (1.92 g, 64%).
64%	Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 1h; Stage #2: (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine In tetrahydrofuran; hexane at 0 - 20℃; for 12h;	1.1 Step 1. tert-Butyl (4S)-2,2-dimethyl-4-vinyl-l,3-oxazolidine-3-carboxylate To a suspension of methyl triphenylphosphonium bromide (5.63 g, 15.8 mmol) in tetrahydrofuran (140 mL) was added 2.5 M n-butyllithium in hexane (7.35 mL, 18.4 mmol). The deep red solution was stirred at 0 °C for 1 h. Then a solution of fert-butyl (4R)-4-formyl-2,2-dimethyl-l,3-oxazolidine-3-carboxylate (from Aldrich, 3.01 g, 13.1 mmol) in tetrahydrofuran (7.3 mL) was added drop wise at 0 °C. The red solution was warmed to room temperature and stirred for 12 h. Hexanes was added to the reaction mixture in 4: 1 (v/v) ratio. The suspension was filtered through Celite and the filtrate concentrated. The resultant residue was purified by flash chromatography (eluting with 10% ethyl acetate in hexanes) to give the desired compound as colorless oil (1.92 g, 64%).
64%	Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 1h; Stage #2: (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine In tetrahydrofuran; hexane at 0 - 20℃; for 12h;	J1.1 tert-Butyl(4S)-2,2-dimethyl-4-vinyl-1,3-oxazolidine-3-carboxylate To a suspension of methyl triphenylphosphonium bromide (5.63 g, 15.8 mmol) in tetrahydrofuran (140 mL) was added 2.5 M n-butyllithium in hexane (7.35 mL, 18.4 mmol). The deep red solution was stirred at 0° C. for 1 h. Then a solution of tert-butyl(4R)-4-formyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (from Aldrich, 3.01 g, 13.1 mmol) in tetrahydrofuran (7.3 mL) was added drop wise at 0° C. The red solution was warmed to room temperature and stirred for 12 h. Hexanes was added to the reaction mixture in 4:1 (v/v) ratio. The suspension was filtered through Celite and the filtrate concentrated. The resultant residue was purified by flash chromatography (eluting with 10% ethyl acetate in hexanes) to give the desired compound as colorless oil (1.92 g, 64%).
	With potassium hexamethylsilazane 1.) THF, toluene, r.t., 1 h, 2.) THF, toluene, -78 deg C to r.t., 2 h; Yield given. Multistep reaction;
	Stage #1: Methyltriphenylphosphonium bromide With sodium hexamethyldisilazane In tetrahydrofuran for 1h; Stage #2: (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine In tetrahydrofuran at -78 - 20℃; for 2.75h;
	Stage #1: Methyltriphenylphosphonium bromide With potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine In tetrahydrofuran for 0.166667h;	Q 3 [(S)- (TERT-BUTOXYCARBONYL)-2, 2-DIMETHYL-4-VINYL-OXAZOLIDINE] To a suspension of Ph3PCH3Br (24.60 g, 68.8 mmol) in anhydrous THF (40 [ML)] is added t- [BUOK] (7.72 g, 68.8 mmol) in one portion at room temperature. After stirring for 10 min, the yellow mixture is treated with a solution of 3 (R)- (tert-butoxycarbonyl) 2,2-dimethyl-4- oxazolidine carboxaldehyde (10.50 g, 45.8 mmol) in THF. The mixture is stirred for additional 10 min and then partitioned between brine and EtOAc. The organic layer is separated and the aqueous layer is extracted with EtOAc (2 x). The combined extracts are dried over MgS04 and evaporated under reduced pressure. The residue is treated with ether and the white solid which forms is removed by filtration. The filtrate is evaporated and the residue is purified by flash chromatography on silica gel using EtOAc-hexanes.

Reference： [1]Keyes, Robert F.; Carter, Justin J.; Zhang, Xiaolin; Ma, Zhenkun [Organic Letters, 2005, vol. 7, # 5, p. 847 - 849]
[2]Current Patent Assignee: AMGEN INC - WO2014/22752, 2014, A1 Location in patent: Page/Page column 168
[3]Current Patent Assignee: USTAV ORGANICKE CHEMIE A BIOCHEMIE AV HACEK OVER HACEK OVER R V V I; CZECH ACADEMY OF SCIENCES; INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY AS CR; THE JOHNS HOPKINS UNIVERSITY - WO2018/144718, 2018, A1 Location in patent: Paragraph 0201
[4]Current Patent Assignee: INCYTE CORP - US2014/121198, 2014, A1 Location in patent: Paragraph 0645; 0646
[5]Current Patent Assignee: INCYTE CORP - WO2015/26818, 2015, A1 Location in patent: Page/Page column 43; 44
[6]Current Patent Assignee: INCYTE CORP - WO2015/157257, 2015, A1 Location in patent: Page/Page column 37
[7]Current Patent Assignee: INCYTE CORP - US2015/361094, 2015, A1 Location in patent: Paragraph 0353
[8]Campbell, Andrew D.; Raynham, Tony M.; Taylor, Richard J. K. [Synthesis, 1998, # 12, p. 1707 - 1709]
[9]Brackmann, Farina; Colombo, Noemi; Cabrele, Chiara; De Meijere, Armin [European Journal of Organic Chemistry, 2006, # 19, p. 4440 - 4450]
[10]Current Patent Assignee: PROCTER & GAMBLE CO - WO2004/14893, 2004, A2 Location in patent: Page 110; 111

5
[ 133625-87-3 ]
(2S)-1-hydroxybut-3-en-2-methylpyrrole-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With hydrogenchloride In 1,4-dioxane; water at 20℃; for 2h;	64-65.2 Step 2: (S)-2-aminobut-3-en-l-ol hydrochloride A solution of (S)-tert-butyl 2,2-dimethyl-4-vinyloxazolidine-3-carboxylate (3.8 g, 16.72 mmol) in 5.0 N aqueous HCl (Sigma Aldrich, 100 ml, 502 mmol) and a 4.0 M solution of HCl in 1,4-dioxane (Sigma Aldrich, 104 ml, 418 mmol) was stirred at RT. Upon addition of the dioxane solution, gas evolution was notable. The reaction was stirred for 2 h at which point the colorless solution was concentrated in vacuo to give a tan oil that was azeotroped with MeOH and toluene. A tan, waxy solid that resulted was dried further under high vacuum, giving (S)-2-aminobut-3-en-l -ol as a hydrochloride salt (1.84 g, 89%): FontWeight="Bold" FontSize="10" H NMR (400 MHz, MeOD) δ ppm 5.81 - 5.95 (1 H, m) 5.39 - 5.54 (2 H, m) 3.73 - 3.86 (2 H, m) 3.51 - 3.65 (1 H, m).
	With hydrogenchloride; water for 0.5h; Ambient temperature; Yield given;

Reference： [1]Current Patent Assignee: AMGEN INC - WO2014/22752, 2014, A1 Location in patent: Page/Page column 168; 169
[2]Campbell, Andrew D.; Raynham, Tony M.; Taylor, Richard J. K. [Synthesis, 1998, # 12, p. 1707 - 1709]

6
[ 109-04-6 ]
[ 133625-87-3 ]
(S)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-[2-(2-pyridinyl)ethyl]oxazolidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	Stage #1: tert-butyl (4S)-2,2-dimethyl-4-vinyl-1,3-oxazolidine-3-carboxylate With 9-borabicyclo[3.3.1]nonane dimer In toluene at 80 - 85℃; Stage #2: 2-bromo-pyridine With sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetra-(n-butyl)ammonium iodide In toluene at 90℃; Further stages.;

Reference： [1]Sabat, Mark; Johnson, Carl R. [Organic Letters, 2000, vol. 2, # 8, p. 1089 - 1091]

7
[ 626-55-1 ]
[ 133625-87-3 ]
(S)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-[2-(3-pyridinyl)ethyl]oxazolidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	Stage #1: tert-butyl (4S)-2,2-dimethyl-4-vinyl-1,3-oxazolidine-3-carboxylate With 9-borabicyclo[3.3.1]nonane dimer In toluene at 80 - 85℃; Stage #2: 3-Bromopyridine With sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetra-(n-butyl)ammonium iodide In toluene at 90℃; Further stages.;

Reference： [1]Sabat, Mark; Johnson, Carl R. [Organic Letters, 2000, vol. 2, # 8, p. 1089 - 1091]

8
[ 4595-59-9 ]
[ 133625-87-3 ]
(S)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-[2-(5-pyrimidyl)ethyl]oxazolidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	Stage #1: tert-butyl (4S)-2,2-dimethyl-4-vinyl-1,3-oxazolidine-3-carboxylate With 9-borabicyclo[3.3.1]nonane dimer In toluene at 80 - 85℃; Stage #2: 5-bromopyrimidine With sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetra-(n-butyl)ammonium iodide In toluene at 90℃; Further stages.;

Reference： [1]Sabat, Mark; Johnson, Carl R. [Organic Letters, 2000, vol. 2, # 8, p. 1089 - 1091]

9
[ 624-28-2 ]
[ 133625-87-3 ]
(S,S)-2,5-bis{2-[3-(tert-butoxycarbonyl-2,2-dimethyl)oxazolidin-4-yl]ethyl}pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	Stage #1: tert-butyl (4S)-2,2-dimethyl-4-vinyl-1,3-oxazolidine-3-carboxylate With 9-borabicyclo[3.3.1]nonane dimer In toluene at 80 - 85℃; Stage #2: 2,5-dibromopyridine With sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetra-(n-butyl)ammonium iodide In toluene at 90℃; Further stages.;

Reference： [1]Sabat, Mark; Johnson, Carl R. [Organic Letters, 2000, vol. 2, # 8, p. 1089 - 1091]

10
[ 92159-87-0 ]
[ 133625-87-3 ]
(S)-4-[2-(4-amino-phenyl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester [ No CAS ]
(S)-4-[2-(4-benzyloxycarbonylaminophenyl)ethyl]-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: tert-butyl (4S)-2,2-dimethyl-4-vinyl-1,3-oxazolidine-3-carboxylate With 9-borabicyclo[3.3.1]nonane dimer In toluene at 80 - 85℃; Stage #2: benzyl (4-bromophenyl)carbamate With sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetra-(n-butyl)ammonium iodide In toluene at 90℃; Further stages.;

Reference： [1]Sabat, Mark; Johnson, Carl R. [Organic Letters, 2000, vol. 2, # 8, p. 1089 - 1091]

11
[ 91103-37-6 ]
[ 77-76-9 ]
[ 133625-87-3 ]

Yield	Reaction Conditions	Operation in experiment
	With boron trifluoride diethyl etherate In acetone at -20 - 20℃;

Reference： [1]Sabat, Mark; Johnson, Carl R. [Organic Letters, 2000, vol. 2, # 8, p. 1089 - 1091]

12
[ 133625-87-3 ]
[ 336130-03-1 ]
[ 336130-04-2 ]

Yield	Reaction Conditions	Operation in experiment
1: 65% 2: 19%	With 3,3-dimethyldioxirane In dichloromethane; acetone at 20℃; for 12h;

Reference： [1]Koviach; Chappell; Halcomb [Journal of Organic Chemistry, 2001, vol. 66, # 7, p. 2318 - 2326]

13
[ 2065-66-9 ]
[ 95715-87-0 ]
[ 133625-87-3 ]

Yield	Reaction Conditions	Operation in experiment
85%	With sodium hexamethyldisilazane In tetrahydrofuran at -25 - 20℃; for 21.5h;
63%	With sodium hexamethyldisilazane In tetrahydrofuran
63%	Stage #1: methyl-triphenylphosphonium iodide With sodium hexamethyldisilazane In tetrahydrofuran at -20℃; for 0.25h; Stage #2: (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine In tetrahydrofuran at -20℃;

Reference： [1]Current Patent Assignee: CRÉDIT INDUSTRIEL ET COMMERCIAL - CIC; BANQUE DE VIZILLE - WO2016/42089, 2016, A1 Location in patent: Page/Page column 171
[2]Banba, Yasunori; Abe, Chiemi; Nemoto, Hideo; Kato, Atsushi; Adachi, Isao; Takahata, Hiroki [Tetrahedron Asymmetry, 2001, vol. 12, # 6, p. 817 - 819]
[3]Takahata, Hiroki; Banba, Yasunori; Ouchi, Hidekazu; Nemoto, Hideo; Kato, Atsushi; Adachi, Isao [Journal of Organic Chemistry, 2003, vol. 68, # 9, p. 3603 - 3607]

14
[ 133625-87-3 ]
[ 91103-37-6 ]

Yield	Reaction Conditions	Operation in experiment
76%	With toluene-4-sulfonic acid In methanol at 0 - 20℃;	19.2 tert-Butyl [(1S)-1-(hydroxymethyl)prop-2-en-1-yl]carbamate To a solution of tert-butyl (4S)-2,2-dimethyl-4-vinyl-1,3-oxazolidine-3-carboxylate (1.90 g, 8.36 mmol) in methanol (83 mL) was added p-toluenesulfonic acid monohydrate (0.80 g, 4.2 mmol) at 0° C. The mixture was slowly warmed to room temperature overnight. The reaction mixture was diluted with saturated NaHCO3 solution, concentrated, and then diluted with ethyl acetate. The organic layer was washed with sat. NaHCO3 (2×) and brine, dried over Na2SO4, filtered and concentrated to give the desired product as colorless oil (1.187 g, 76%). 1H NMR (400 MHz, CDCl3) δ 5.81 (1H, m), 5.25 (2H, m), 4.90 (1H, m), 4.25 (1H, br s), 3.67 (2H, m), 1.45 (9H, s) ppm.
76%	With toluene-4-sulfonic acid In methanol at 0 - 20℃;	J1.2 Step 2. tert-Butyl [(1S)-1-(hydroxymethyl)prop-2-en-1-ylJcarbamate Step 2. tert-Butyl [(1S)-1-(hydroxymethyl)prop-2-en-1-ylJcarbamateTo a solution of tert-butyl (4S)-2,2-dimethyl-4-vinyl- 1,3 -oxazolidine-3 -carboxylate (1.90 g, 8.36 mmol) in methanol (83 mL) was addedp-toluenesulfonicacid monohydrate (0.80 g, 4.2 mmol) at 0 °C. The mixture was slowly warmed to room temperature overnight. The reaction mixture was diluted with saturated NaHCO3 solution, concentrated, and then diluted with ethyl acetate. The organic layer was washed with sat. NaHCO3 (2x) and brine, dried over Na2SO4, filtered andconcentrated to give the desired product as colorless oil (1.187 g, 76%). ‘H NMR (400 MHz, CDC13) 5.81 (1H, m), 5.25 (2H, m), 4.90 (1H, m), 4.25 (1H, br s), 3.67 (2H, m), 1.45 (9H, s) ppm.
76%	With toluene-4-sulfonic acid In methanol at 0 - 20℃;	1.2 Step 2. tert-Butyl [(IS)- l-(hydroxymethyl)prop-2-en-l-yl] carbamate To a solution of tert-butyl (4S)-2,2-dimethyl-4-vinyl-l,3-oxazolidine-3- carboxylate (1.90 g, 8.36 mmol) in methanol (83 mL) was added /?-toluenesulfonic acid monohydrate (0.80 g, 4.2 mmol) at 0 °C. The mixture was slowly warmed to room temperature overnight. The reaction mixture was diluted with saturated NaHCCte solution, concentrated, and then diluted with ethyl acetate. The organic layer was washed with sat. NaHCC"3 (2x) and brine, dried over Na2S04, filtered and concentrated to give the desired product as colorless oil (1.187 g, 76%). NMR (400 MHz, CDCb) δ 5.81 (1H, m), 5.25 (2H, m), 4.90 (1H, m), 4.25 (1H, br s), 3.67 (2H, m), 1.45 (9H, s) ppm.

76%	With toluene-4-sulfonic acid In methanol; water at 0 - 20℃;	J1.2 tert-Butyl[(1S)-1-(hydroxymethyl)prop-2-en-1-yl]carbamate To a solution of tert-butyl(4S)-2,2-dimethyl-4-vinyl-1,3-oxazolidine-3-carboxylate (1.90 g, 8.36 mmol) in methanol (83 mL) was added p-toluenesulfonic acid monohydrate (0.80 g, 4.2 mmol) at 0° C. The mixture was slowly warmed to room temperature overnight. The reaction mixture was diluted with saturated NaHCO3 solution, concentrated, and then diluted with ethyl acetate. The organic layer was washed with sat. NaHCO3 (2×) and brine, dried over Na2SO4, filtered and concentrated to give the desired product as colorless oil (1.187 g, 76%). 1H NMR (400 MHz, CDCl3) δ 5.81 (1H, m), 5.25 (2H, m), 4.90 (1H, m), 4.25 (1H, br s), 3.67 (2H, m), 1.45 (9H, s) ppm.
	With toluene-4-sulfonic acid In methanol
	With Dowex-M₄₃ In methanol; water at 20℃; for 9h;
	With toluene-4-sulfonic acid In methanol; water for 17h;
	With toluene-4-sulfonic acid In methanol for 2h; Heating / reflux;	Q [2 (S)-TERT-BUTOXYCARBONYLAMINO-3-BUTEN-L-OL] A solution of 3 [(S)- (TERT-BUTOXYCARBONYL)-2,] 2-dimethyl-4vinyl-oxazolidine (10.50 g, 46.3 mmol) and p-TsOH, H20 (0.88 g, 4.6 mmol) in [MEOH] (100 mL) is heated at reflux for 2 days. After cooling, the solvent is evaporated and the residue is purified by flash chromatography on silica gel using EtOAc-hexanes.
	With toluene-4-sulfonic acid In methanol at 20℃; for 16h;

Reference： [1]Current Patent Assignee: INCYTE CORP - US2014/121198, 2014, A1 Location in patent: Paragraph 0645; 0647
[2]Current Patent Assignee: INCYTE CORP - WO2015/26818, 2015, A1 Location in patent: Page/Page column 44
[3]Current Patent Assignee: INCYTE CORP - WO2015/157257, 2015, A1 Location in patent: Page/Page column 37; 38
[4]Current Patent Assignee: INCYTE CORP - US2015/361094, 2015, A1 Location in patent: Paragraph 0354
[5]Banba, Yasunori; Abe, Chiemi; Nemoto, Hideo; Kato, Atsushi; Adachi, Isao; Takahata, Hiroki [Tetrahedron Asymmetry, 2001, vol. 12, # 6, p. 817 - 819]
[6]Keyes, Robert F.; Carter, Justin J.; Zhang, Xiaolin; Ma, Zhenkun [Organic Letters, 2005, vol. 7, # 5, p. 847 - 849]
[7]Brackmann, Farina; Colombo, Noemi; Cabrele, Chiara; De Meijere, Armin [European Journal of Organic Chemistry, 2006, # 19, p. 4440 - 4450]
[8]Current Patent Assignee: PROCTER & GAMBLE CO - WO2004/14893, 2004, A2 Location in patent: Page 110; 111
[9]Current Patent Assignee: BANQUE DE VIZILLE; CRÉDIT INDUSTRIEL ET COMMERCIAL - CIC - WO2016/42089, 2016, A1 Location in patent: Page/Page column 171; 172

15
tert-butyl 4-formyl-2,2-dimethyloxazolidine-3-carboxylate [ No CAS ]
[ 18107-18-1 ]
[ 115378-31-9 ]
[ 133625-87-3 ]

Yield	Reaction Conditions	Operation in experiment
	With Rh(PPh₃)3Cl; triphenylphosphine In tetrahydrofuran; isopropyl alcohol at 25℃; for 4h; Title compound not separated from byproducts;

Reference： [1]Lebel, Heandleandne; Paquet, Valeandrie; Proulx, Caroline [Angewandte Chemie - International Edition, 2001, vol. 40, # 15, p. 2887 - 2890]

16
[ 133625-87-3 ]
[ 112219-66-6 ]
(E/Z)-5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-1-O,2-N-isopropylidene-2-(tert-butoxycarbonylamino)-D-erythro-L-galacto-dec-3-enitol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
16%	In tetrachloromethane at 100℃; for 3.5h;

Reference： [1]Dondoni; Giovannini; Marra [Journal of the Chemical Society. Perkin Transactions 1 (2001), 2001, # 19, p. 2380 - 2388]

17
[ 133625-87-3 ]
[ 82659-55-0 ]
(E/Z)-6,10-anhydro-7,8,9,11-tetra-O-benzyl-2,3,4,5-tetradeoxy-1-O,2-N-isopropylidene-2-(tert-butoxycarbonylamino)-D-threo-L-gulo-undec-3-enitol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	In tetrachloromethane at 100℃; for 3.5h;

Reference： [1]Dondoni; Giovannini; Marra [Journal of the Chemical Society. Perkin Transactions 1 (2001), 2001, # 19, p. 2380 - 2388]

18
[ 133625-87-3 ]
[ 405071-89-8 ]
6,10:13,17-dianhydro-7,8,9,14,15,16,18-hepta-O-benzyl-2,3,4,5,11,12-hexadeoxy-1-O,2-N-isopropylidene-2-(tert-butoxycarbonylamino)-D-arabino-D-allo-L-gulo-octadec-3-enitol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	In tetrachloromethane at 100℃; for 3.5h;

Reference： [1]Dondoni; Giovannini; Marra [Journal of the Chemical Society. Perkin Transactions 1 (2001), 2001, # 19, p. 2380 - 2388]

19
[ 133625-87-3 ]
[ 606970-33-6 ]
(2R,3R,4R,5S,6R)-3,5-Diacetoxy-4-benzyloxy-2-benzyloxymethyl-6-[(E)-3-((S)-3-tert-butoxycarbonyl-2,2-dimethyl-oxazolidin-4-yl)-allyl]-piperidine-1-carboxylic acid 2,2,2-trichloro-ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	In dichloromethane at 40℃;

Reference： [1]Godin, Guillaume; Compain, Philippe; Martin, Olivier R. [Organic Letters, 2003, vol. 5, # 18, p. 3269 - 3272]

20
[ 860264-36-4 ]
[ 133625-87-3 ]
(Z)-6,9-anhydro-7,8,10-tri-O-benzyl-6-N-benzyloxycarbonylamino-2-tert-butoxycarbonylamino-2,3,4,5,6-pentadeoxy-1-O,2-N-isopropylidene-D-talo-D-glycero-dec-3-enitol [ No CAS ]
(E)-6,9-anhydro-7,8,10-tri-O-benzyl-6-N-benzyloxycarbonylamino-2-tert-butoxycarbonylamino-2,3,4,5,6-pentadeoxy-1-O,2-N-isopropylidene-D-talo-D-glycero-dec-3-enitol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane at 40℃; for 18h; Title compound not separated from byproducts;

Reference： [1]Dondoni, Alessandro; Giovannini, Pier Paolo; Perrone, Daniela [Journal of Organic Chemistry, 2005, vol. 70, # 14, p. 5508 - 5518]

21
[ 860264-37-5 ]
[ 133625-87-3 ]
(Z)-6,9-anhydro-7,8,10-tri-O-benzyl-6-N-benzyloxycarbonylamino-2-tert-butoxycarbonylamino-2,3,4,5,6-pentadeoxy-1-O,2-N-isopropylidene-D-manno-L-glycero-dec-3-enitol [ No CAS ]
(E)-6,9-anhydro-7,8,10-tri-O-benzyl-6-N-benzyloxycarbonylamino-2-tert-butoxycarbonylamino-2,3,4,5,6-pentadeoxy-1-O,2-N-isopropylidene-D-manno-L-glycero-dec-3-enitol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane at 40℃; for 18h; Title compound not separated from byproducts;

Reference： [1]Dondoni, Alessandro; Giovannini, Pier Paolo; Perrone, Daniela [Journal of Organic Chemistry, 2005, vol. 70, # 14, p. 5508 - 5518]

22
[ 860264-34-2 ]
[ 133625-87-3 ]
6,10-anhydro-7,8,9,11-tetra-O-benzyl-6-N-benzyloxycarbonylamino-2-tert-butoxycarbonylamino-2,3,4,5,6-pentadeoxy-1-O,2-N-isopropylidene-L-erythro-L-galacto-undec-3-enitol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	In dichloromethane at 40℃; for 18h;

Reference： [1]Dondoni, Alessandro; Giovannini, Pier Paolo; Perrone, Daniela [Journal of Organic Chemistry, 2005, vol. 70, # 14, p. 5508 - 5518]

23
[ 860264-35-3 ]
[ 133625-87-3 ]
6,10-anhydro-7,8,9,11-tetra-O-benzyl-6-N-benzyloxycarbonylamino-2-tert-butoxycarbonylamino-2,3,4,5,6-pentadeoxy-1-O,2-N-isopropylidene-L-threo-L-galacto-undec-3-enitol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	In dichloromethane at 40℃; for 18h;

Reference： [1]Dondoni, Alessandro; Giovannini, Pier Paolo; Perrone, Daniela [Journal of Organic Chemistry, 2005, vol. 70, # 14, p. 5508 - 5518]

24
[ 133625-87-3 ]
[ 91028-39-6 ]

Yield	Reaction Conditions	Operation in experiment
	With jones reagent In acetone at 0 - 20℃; for 4.5h;

Reference： [1]Dondoni, Alessandro; Giovannini, Pier Paolo; Perrone, Daniela [Journal of Organic Chemistry, 2005, vol. 70, # 14, p. 5508 - 5518]

25
[ 133625-87-3 ]
6-amino-2-hydroxymethyl-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: p-toluenesulfonic acidH₂O / methanol; H₂O / 17 h 2: imidazole / dimethylformamide / 2.5 h 3: KOtBu / dimethylformamide / 0.25 h / -20 °C 4: Grubbs I catalyst / CH₂Cl₂ / 17 h 5: cyclohexylmagnesium bromide; MeTi(OiPr)3 / diethyl ether; tetrahydrofuran / 19 h 6: tetrabutylammonium fluoride3H₂O / tetrahydrofuran / 3.5 h 7: H₂ / 10 percent Pd/C / methanol / 17 h

Reference： [1]Brackmann, Farina; Colombo, Noemi; Cabrele, Chiara; De Meijere, Armin [European Journal of Organic Chemistry, 2006, # 19, p. 4440 - 4450]

26
[ 133625-87-3 ]
(2S,1'R,3R,4R)-Nα-Boc-3,4-(dibenzylaminomethano)prolinol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: p-toluenesulfonic acidH₂O / methanol; H₂O / 17 h 2: imidazole / dimethylformamide / 2.5 h 3: KOtBu / dimethylformamide / 0.25 h / -20 °C 4: Grubbs I catalyst / CH₂Cl₂ / 17 h 5: cyclohexylmagnesium bromide; MeTi(OiPr)3 / diethyl ether; tetrahydrofuran / 19 h 6: tetrabutylammonium fluoride3H₂O / tetrahydrofuran / 3.5 h

Reference： [1]Brackmann, Farina; Colombo, Noemi; Cabrele, Chiara; De Meijere, Armin [European Journal of Organic Chemistry, 2006, # 19, p. 4440 - 4450]

27
[ 133625-87-3 ]
(2S,1'R,3R,4R)-Nα-Boc-O-tert-butyldimethylsilyl-3,4-(dibenzylaminomethano)prolinol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: p-toluenesulfonic acid*H₂O / methanol; H₂O / 17 h 2: imidazole / dimethylformamide / 2.5 h 3: KOtBu / dimethylformamide / 0.25 h / -20 °C 4: Grubbs I catalyst / CH₂Cl₂ / 17 h 5: cyclohexylmagnesium bromide; MeTi(OiPr)3 / diethyl ether; tetrahydrofuran / 19 h

Reference： [1]Brackmann, Farina; Colombo, Noemi; Cabrele, Chiara; De Meijere, Armin [European Journal of Organic Chemistry, 2006, # 19, p. 4440 - 4450]

28
[ 133625-87-3 ]
[ 247200-49-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: p-toluenesulfonic acid*H₂O / methanol; H₂O / 17 h 2: imidazole / dimethylformamide / 2.5 h 3: KOtBu / dimethylformamide / 0.25 h / -20 °C 4: Grubbs I catalyst / CH₂Cl₂ / 17 h

Reference： [1]Brackmann, Farina; Colombo, Noemi; Cabrele, Chiara; De Meijere, Armin [European Journal of Organic Chemistry, 2006, # 19, p. 4440 - 4450]

29
[ 133625-87-3 ]
[ 860264-43-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 50 percent / Grubbs second generation catalyst / CH₂Cl₂ / 18 h / 40 °C 2: 82 percent / toluene-p-sulfonylhydrazide; aq. AcONa / 1,2-dimethoxy-ethane / 85 °C

Reference： [1]Dondoni, Alessandro; Giovannini, Pier Paolo; Perrone, Daniela [Journal of Organic Chemistry, 2005, vol. 70, # 14, p. 5508 - 5518]

30
[ 133625-87-3 ]
[ 860264-44-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 40 percent / Grubbs second generation catalyst / CH₂Cl₂ / 18 h / 40 °C 2: 71 percent / toluene-p-sulfonylhydrazide; aq. AcONa / 1,2-dimethoxy-ethane / 85 °C

Reference： [1]Dondoni, Alessandro; Giovannini, Pier Paolo; Perrone, Daniela [Journal of Organic Chemistry, 2005, vol. 70, # 14, p. 5508 - 5518]

31
[ 133625-87-3 ]
[ 860264-47-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 50 percent / Grubbs second generation catalyst / CH₂Cl₂ / 18 h / 40 °C 2: 82 percent / toluene-p-sulfonylhydrazide; aq. AcONa / 1,2-dimethoxy-ethane / 85 °C 3: Jones reagent / acetone / 3.5 h / 0 - 20 °C

Reference： [1]Dondoni, Alessandro; Giovannini, Pier Paolo; Perrone, Daniela [Journal of Organic Chemistry, 2005, vol. 70, # 14, p. 5508 - 5518]

32
[ 133625-87-3 ]
(2S,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-((S)-4-tert-butoxycarbonylamino-4-carboxy-butyl)-piperidine-1-carboxylic acid benzyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 40 percent / Grubbs second generation catalyst / CH₂Cl₂ / 18 h / 40 °C 2: 71 percent / toluene-p-sulfonylhydrazide; aq. AcONa / 1,2-dimethoxy-ethane / 85 °C 3: Jones reagent / acetone / 3.5 h / 0 - 20 °C

Reference： [1]Dondoni, Alessandro; Giovannini, Pier Paolo; Perrone, Daniela [Journal of Organic Chemistry, 2005, vol. 70, # 14, p. 5508 - 5518]

33
[ 133625-87-3 ]
methyl (E)-6,10-anhydro-7,8,9,11-tetra-O-benzyl-6-N-benzyloxycarbonylamino-2-tert-butoxycarbonylamino-2,3,4,5,6-pentadeoxy-L-erythro-L-galacto-undec-3-enoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: Jones reagent / acetone / 4.5 h / 0 - 20 °C 2: 62 mg / diethyl ether; methanol / 0.17 h / 0 °C 3: Grubbs second generation catalyst / CH₂Cl₂ / 18 h / 40 °C

Reference： [1]Dondoni, Alessandro; Giovannini, Pier Paolo; Perrone, Daniela [Journal of Organic Chemistry, 2005, vol. 70, # 14, p. 5508 - 5518]

34
[ 133625-87-3 ]
methyl 6,10-anhydro-7,8,9,11-tetra-O-benzyl-6-N-benzyloxycarbonylamino-2-tert-butoxycarbonylamino-2,3,4,5,6-pentadeoxy-L-threo-L-galacto-undeconate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 40 percent / Grubbs second generation catalyst / CH₂Cl₂ / 18 h / 40 °C 2: 71 percent / toluene-p-sulfonylhydrazide; aq. AcONa / 1,2-dimethoxy-ethane / 85 °C 3: Jones reagent / acetone / 3.5 h / 0 - 20 °C 4: diethyl ether; methanol / 0.17 h / 0 °C

Reference： [1]Dondoni, Alessandro; Giovannini, Pier Paolo; Perrone, Daniela [Journal of Organic Chemistry, 2005, vol. 70, # 14, p. 5508 - 5518]

35
[ 133625-87-3 ]
[ 860264-66-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 50 percent / Grubbs second generation catalyst / CH₂Cl₂ / 18 h / 40 °C 2: 82 percent / toluene-p-sulfonylhydrazide; aq. AcONa / 1,2-dimethoxy-ethane / 85 °C 3: Jones reagent / acetone / 3.5 h / 0 - 20 °C 4: 80 percent / PyBOP; DIPEA / CH₂Cl₂ / 2 h / 20 °C

Reference： [1]Dondoni, Alessandro; Giovannini, Pier Paolo; Perrone, Daniela [Journal of Organic Chemistry, 2005, vol. 70, # 14, p. 5508 - 5518]

36
[ 133625-87-3 ]
(2R,3S,4R,5R,6S,8R,4'R)-5-azido-8-(3'-tert-butoxycarbonyl-2',2'-dimethyloxazolidin-4'-yl)-3,4-dihydroxy-2-hydroxymethyl-1,7-dioxaspiro[5.5]undec-10-ene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1.1: 19 percent / dimethyldioxirane / CH₂Cl₂; acetone / 12 h / 20 °C 2.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / 0 °C 2.2: 90 percent / BF₃*Et₂O / tetrahydrofuran; hexane / 1 h / -78 °C 3.1: 91 percent / TBAF; AcOH / tetrahydrofuran / 20 h / 20 °C 4.1: 92 percent / acetonitrile / 12 h / 20 °C 5.1: TMEDA; n-BuLi / tetrahydrofuran; hexane / 1.5 h / -78 °C 5.2: 62 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C 6.1: 45 percent / H₂ / Pd/C / ethyl acetate; methanol / 48 h / 20 °C / 690 Torr 7.1: 51 percent / CSA / CH₂Cl₂ / 20 h / 20 °C 8.1: 85 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

Reference： [1]Koviach; Chappell; Halcomb [Journal of Organic Chemistry, 2001, vol. 66, # 7, p. 2318 - 2326]

37
[ 133625-87-3 ]
(2R,3S,4R,5R,6S,8S,4'R)-5-azido-8-(3'-tert-butoxycarbonyl-2',2'-dimethyloxazolidin-4'-yl)-3,4-dihydroxy-2-hydroxymethyl-1,7-dioxaspiro[5.5]undec-10-ene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1.1: 65 percent / dimethyldioxirane / CH₂Cl₂; acetone / 12 h / 20 °C 2.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / 0 °C 2.2: 90 percent / BF₃*Et₂O / tetrahydrofuran; hexane / 1 h / -78 °C 3.1: 97 percent / TBAF; AcOH / tetrahydrofuran / 20 h / 20 °C 4.1: 100 percent / acetonitrile / 12 h / 20 °C 5.1: TMEDA; n-BuLi / tetrahydrofuran; hexane / 1.5 h / -78 °C 5.2: 77 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C 6.1: 53 percent / H₂ / Pd/C / ethyl acetate; methanol / 72 h / 20 °C / 690 Torr 7.1: 79 percent / CSA / CH₂Cl₂ / 20 h / 20 °C 8.1: 90 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

Reference： [1]Koviach; Chappell; Halcomb [Journal of Organic Chemistry, 2001, vol. 66, # 7, p. 2318 - 2326]

38
[ 133625-87-3 ]
(2R,3S,4R,5R,6S,8R,4'R)-2-acetoxymethyl-5-azido-8-(3'-tert-butoxycarbonyl-2',2'-dimethyloxazolidin-4'-yl)-3,4-diacetoxy-1,7-dioxaspiro[5.5]undec-10-ene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1.1: 19 percent / dimethyldioxirane / CH₂Cl₂; acetone / 12 h / 20 °C 2.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / 0 °C 2.2: 90 percent / BF₃*Et₂O / tetrahydrofuran; hexane / 1 h / -78 °C 3.1: 91 percent / TBAF; AcOH / tetrahydrofuran / 20 h / 20 °C 4.1: 92 percent / acetonitrile / 12 h / 20 °C 5.1: TMEDA; n-BuLi / tetrahydrofuran; hexane / 1.5 h / -78 °C 5.2: 62 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C 6.1: 45 percent / H₂ / Pd/C / ethyl acetate; methanol / 48 h / 20 °C / 690 Torr 7.1: 51 percent / CSA / CH₂Cl₂ / 20 h / 20 °C 8.1: 85 percent / TBAF / tetrahydrofuran / 2 h / 20 °C 9.1: 100 percent / pyridine / 20 °C

Reference： [1]Koviach; Chappell; Halcomb [Journal of Organic Chemistry, 2001, vol. 66, # 7, p. 2318 - 2326]

39
[ 133625-87-3 ]
(2R,3S,4R,5R,6S,8S,4'R)-2-acetoxymethyl-5-azido-8-(3'-tert-butoxycarbonyl-2',2'-dimethyloxazolidin-4'-yl)-3,4-diacetoxy-1,7-dioxaspiro[5.5]undec-10-ene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1.1: 65 percent / dimethyldioxirane / CH₂Cl₂; acetone / 12 h / 20 °C 2.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / 0 °C 2.2: 90 percent / BF₃*Et₂O / tetrahydrofuran; hexane / 1 h / -78 °C 3.1: 97 percent / TBAF; AcOH / tetrahydrofuran / 20 h / 20 °C 4.1: 100 percent / acetonitrile / 12 h / 20 °C 5.1: TMEDA; n-BuLi / tetrahydrofuran; hexane / 1.5 h / -78 °C 5.2: 77 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C 6.1: 53 percent / H₂ / Pd/C / ethyl acetate; methanol / 72 h / 20 °C / 690 Torr 7.1: 79 percent / CSA / CH₂Cl₂ / 20 h / 20 °C 8.1: 90 percent / TBAF / tetrahydrofuran / 2 h / 20 °C 9.1: 100 percent / pyridine / 20 °C

Reference： [1]Koviach; Chappell; Halcomb [Journal of Organic Chemistry, 2001, vol. 66, # 7, p. 2318 - 2326]

40
[ 133625-87-3 ]
(2R,3S,4R,5R,6S,8R,4'R)-5-acetamido-2-acetoxymethyl-8-(3'-tert-butoxycarbonyl-2',2'-dimethyloxazolidin-4'-yl)-3,4-diacetoxy-1,7-dioxaspiro[5.5]undecane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1.1: 19 percent / dimethyldioxirane / CH₂Cl₂; acetone / 12 h / 20 °C 2.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / 0 °C 2.2: 90 percent / BF₃*Et₂O / tetrahydrofuran; hexane / 1 h / -78 °C 3.1: 91 percent / TBAF; AcOH / tetrahydrofuran / 20 h / 20 °C 4.1: 92 percent / acetonitrile / 12 h / 20 °C 5.1: TMEDA; n-BuLi / tetrahydrofuran; hexane / 1.5 h / -78 °C 5.2: 62 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C 6.1: 45 percent / H₂ / Pd/C / ethyl acetate; methanol / 48 h / 20 °C / 690 Torr 7.1: 51 percent / CSA / CH₂Cl₂ / 20 h / 20 °C 8.1: 85 percent / TBAF / tetrahydrofuran / 2 h / 20 °C 9.1: 100 percent / pyridine / 20 °C 10.1: 45 percent / H₂ / Pd/C / methanol / 20 h / 20 °C

Reference： [1]Koviach; Chappell; Halcomb [Journal of Organic Chemistry, 2001, vol. 66, # 7, p. 2318 - 2326]

41
[ 133625-87-3 ]
(2R,3S,4R,5R,6S,8S,4'R)-5-acetamido-2-acetoxymethyl-8-(3'-tert-butoxycarbonyl-2',2'-dimethyloxazolidin-4'-yl)-3,4-diacetoxy-1,7-dioxaspiro[5.5]undecane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1.1: 65 percent / dimethyldioxirane / CH₂Cl₂; acetone / 12 h / 20 °C 2.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / 0 °C 2.2: 90 percent / BF₃*Et₂O / tetrahydrofuran; hexane / 1 h / -78 °C 3.1: 97 percent / TBAF; AcOH / tetrahydrofuran / 20 h / 20 °C 4.1: 100 percent / acetonitrile / 12 h / 20 °C 5.1: TMEDA; n-BuLi / tetrahydrofuran; hexane / 1.5 h / -78 °C 5.2: 77 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C 6.1: 53 percent / H₂ / Pd/C / ethyl acetate; methanol / 72 h / 20 °C / 690 Torr 7.1: 79 percent / CSA / CH₂Cl₂ / 20 h / 20 °C 8.1: 90 percent / TBAF / tetrahydrofuran / 2 h / 20 °C 9.1: 100 percent / pyridine / 20 °C 10.1: 45 percent / H₂ / Pd/C / methanol / 20 h / 20 °C

Reference： [1]Koviach; Chappell; Halcomb [Journal of Organic Chemistry, 2001, vol. 66, # 7, p. 2318 - 2326]

42
[ 133625-87-3 ]
(2R,3S,4R,5R,6S,8R,4'R)-5-azido-8-(3'-tert-butoxycarbonyl-2',2'-dimethyloxazolidin-4'-yl)-3,4-di-tert-butyldimethylsilyloxy-2-tert-butyldiphenylsilyloxymethyl-1,7-dioxaspiro[5.5]undec-10-ene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: 19 percent / dimethyldioxirane / CH₂Cl₂; acetone / 12 h / 20 °C 2.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / 0 °C 2.2: 90 percent / BF₃*Et₂O / tetrahydrofuran; hexane / 1 h / -78 °C 3.1: 91 percent / TBAF; AcOH / tetrahydrofuran / 20 h / 20 °C 4.1: 92 percent / acetonitrile / 12 h / 20 °C 5.1: TMEDA; n-BuLi / tetrahydrofuran; hexane / 1.5 h / -78 °C 5.2: 62 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C 6.1: 45 percent / H₂ / Pd/C / ethyl acetate; methanol / 48 h / 20 °C / 690 Torr 7.1: 51 percent / CSA / CH₂Cl₂ / 20 h / 20 °C

Reference： [1]Koviach; Chappell; Halcomb [Journal of Organic Chemistry, 2001, vol. 66, # 7, p. 2318 - 2326]

43
[ 133625-87-3 ]
(2R,3S,4R,5R,6S,8S,4'R)-5-azido-8-(3'-tert-butoxycarbonyl-2',2'-dimethyloxazolidin-4'-yl)-3,4-di-tert-butyldimethylsilyloxy-2-tert-butyldiphenylsilyloxymethyl-1,7-dioxaspiro[5.5]undec-10-ene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: 65 percent / dimethyldioxirane / CH₂Cl₂; acetone / 12 h / 20 °C 2.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / 0 °C 2.2: 90 percent / BF₃*Et₂O / tetrahydrofuran; hexane / 1 h / -78 °C 3.1: 97 percent / TBAF; AcOH / tetrahydrofuran / 20 h / 20 °C 4.1: 100 percent / acetonitrile / 12 h / 20 °C 5.1: TMEDA; n-BuLi / tetrahydrofuran; hexane / 1.5 h / -78 °C 5.2: 77 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C 6.1: 53 percent / H₂ / Pd/C / ethyl acetate; methanol / 72 h / 20 °C / 690 Torr 7.1: 79 percent / CSA / CH₂Cl₂ / 20 h / 20 °C

Reference： [1]Koviach; Chappell; Halcomb [Journal of Organic Chemistry, 2001, vol. 66, # 7, p. 2318 - 2326]

44
[ 133625-87-3 ]
(4'S,4''R)-2-azido-1-C-[4'-(3'-tert-butoxycarbonyl-2'',2''-dimethyloxazolidin-4''-yl)-4'-trimethylsilyloxy-1'-Z-butenyl]-3,4-di-O-(tert-butyldimethylsilyl)-6-O-(tert-butyldiphenylsilyl)-2-deoxy-α,β-D-galactopyranose [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: 65 percent / dimethyldioxirane / CH₂Cl₂; acetone / 12 h / 20 °C 2.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / 0 °C 2.2: 90 percent / BF₃*Et₂O / tetrahydrofuran; hexane / 1 h / -78 °C 3.1: 97 percent / TBAF; AcOH / tetrahydrofuran / 20 h / 20 °C 4.1: 100 percent / acetonitrile / 12 h / 20 °C 5.1: TMEDA; n-BuLi / tetrahydrofuran; hexane / 1.5 h / -78 °C 5.2: 77 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C 6.1: 53 percent / H₂ / Pd/C / ethyl acetate; methanol / 72 h / 20 °C / 690 Torr

Reference： [1]Koviach; Chappell; Halcomb [Journal of Organic Chemistry, 2001, vol. 66, # 7, p. 2318 - 2326]

45
[ 133625-87-3 ]
(4'R,4''R)-2-azido-1-C-[4'-(3'-tert-butoxycarbonyl-2'',2''-dimethyloxazolidin-4''-yl)-4'-trimethylsilyloxy-1'-Z-butenyl]-3,4-di-O-(tert-butyldimethylsilyl)-6-O-(tert-butyldiphenylsilyl)-2-deoxy-α,β-D-galactopyranose [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: 19 percent / dimethyldioxirane / CH₂Cl₂; acetone / 12 h / 20 °C 2.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / 0 °C 2.2: 90 percent / BF₃*Et₂O / tetrahydrofuran; hexane / 1 h / -78 °C 3.1: 91 percent / TBAF; AcOH / tetrahydrofuran / 20 h / 20 °C 4.1: 92 percent / acetonitrile / 12 h / 20 °C 5.1: TMEDA; n-BuLi / tetrahydrofuran; hexane / 1.5 h / -78 °C 5.2: 62 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C 6.1: 45 percent / H₂ / Pd/C / ethyl acetate; methanol / 48 h / 20 °C / 690 Torr

Reference： [1]Koviach; Chappell; Halcomb [Journal of Organic Chemistry, 2001, vol. 66, # 7, p. 2318 - 2326]

46
[ 133625-87-3 ]
[ 147959-19-1 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1997,vol. 45,p. 2116 - 2118

47
[ 51372-93-1 ]
[ 133625-87-3 ]

Reference： [1]Tetrahedron Letters,1997,vol. 38,p. 6779 - 6780

48
[ 74213-24-4 ]
[ 133625-87-3 ]
[ 1020071-18-4 ]
[ 1020071-17-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate In ethyl acetate at 20℃;
30 % de	With sodium hydrogencarbonate In ethyl acetate Overall yield = 86 %;

Reference： [1]Pinto, Andrea; Conti, Paola; De Amici, Marco; Tamborini, Lucia; Madsen, Ulf; Nielsen, Birgitte; Christesen, Thomas; Bräuner-Osborne, Hans; De Micheli, Carlo [Journal of Medicinal Chemistry, 2008, vol. 51, # 7, p. 2311 - 2315]
[2]Tamborini, Lucia; Pinto, Andrea; Iannuzzi, Maria C.; DeMicheli, Carlo; Conti, Paola; Smith, Terry K.; Major, Louise L.; Cosconati, Sandro; Marinelli, Luciana; Novellino, Ettore; LoPresti, Leonardo; Wong, Pui E.; Barrett, Michael P. [ChemMedChem, 2012, vol. 7, # 9, p. 1623 - 1634,12]

49
[ 766-77-8 ]
[ 133625-87-3 ]
[ 1205639-49-1 ]

Yield	Reaction Conditions	Operation in experiment
95%	at 20℃;	43.a (S)-2,2-Dimethyl-4-vinyl-oxazolidine-3-carboxylic acid tert-butyl ester (750 mg; CAS 133625-87-3) was dissolved in dimethylphenylsilane (25 ml), platinum(IV)-oxide (187 mg) was added and the mixture was stirred overnight at room temperature. The catalyst was filtered off and the filtrate was evaporated in vacuo. The crude product was purified by column chromatography (SiO2; heptane/ethyl acetate=4:1) to give (S)-4-[2-(dimethyl-phenyl-silanyl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (1.14 g, 95%) as colourless oil, which was used directly for the next step.

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - US2010/29589, 2010, A1 Location in patent: Page/Page column 41

50
[ 167466-67-3 ]
[ 133625-87-3 ]
(S)-(tert-butyl) 4-((R)-5-(benzyloxy)-4-(benzyloxycarbonylamino)-5-oxopent-1-enyl)-2,2-dimethyloxazolidine-3-carboxylate [ No CAS ]
[ 1423076-19-0 ]
[ 1423076-20-3 ]

Yield	Reaction Conditions	Operation in experiment
1: 56% 2: 17 mg 3: 22%	With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane for 7h; Reflux;

Reference： [1]Saito, Yukako; Yoshimura, Yuichi; Wakamatsu, Hideaki; Takahata, Hiroki [Molecules, 2013, vol. 18, # 1, p. 1162 - 1173]

51
[ 1535192-89-2 ]
[ 133625-87-3 ]
[ 1535192-92-7 ]
di-tert-butyl (9,9'-((3aS,3a'S,4R,4'R,6S,6aR,6'S,6a'R)-6,6'-((E)-hex-3-ene-1,6-diyl)bis(2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxole-6,4-diyl))bis(9H-purine-9,6-diyl))bis(tert-butoxycarbonylcarbamate) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 61% 2: 37%	With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 20℃; Inert atmosphere; Reflux;	6 4.1.6. (S)-tert-Butyl 4-((E)-4-((3aR,4S,6R,6aS)-6-(6-(bis(tert-butoxycarbonyl)amino)-9H-purin-9-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)but-1-enyl)-2,2-dimethyloxazolidine-3-carboxylate (20) To a solution of 16 (0.31 g, 0.58 mmol) and 19 (0.13 g, 0.58 mmol) in dry DCM (40 mL) was added second generation Grubbs catalyst (10 mg) at room temperature under N2. The reaction mixture was stirred for 8 h at room temperature and heated to reflux overnight. The mixture was filtered through Celite, and the solvent removed under reduced pressure. The residue was purified by silica gel column chromatography (hexanes/EtOAc=2:1) to give 20 (0.26 g, 61%) as white foam, 21 (0.11 g, 37%) as by-product; 1H NMR (400 MHz, CDCl3) δ 8.78 (s, 1H), 8.04 (s, 1H), 5.52 (m, 1H), 5.43 (dd, J=7.2, 15.4 MHz, 1H), 5.03 (t, J=6.0 Hz, 1H), 4.71 (td, J=11.6, 6.0 Hz, 1H), 4.45 (t, J=6.4 Hz, 1H), 4.24 (m, 1H), 3.96 (dd, J=6, 8.8 Hz, 1H), 3.66 (dd, J=2.0, 8.8 Hz, 1H), 2.42 (m, 1H), 2.25 (m, 1H), 2.15-2.08 (m, 3H), 1.69 (m, 1H), 1.53 (m, 1H), 1.49 (s, 3H), 1.44 (s, 3H), 1.406 (s, 30H), 1.25 (s, 3H); 13C NMR (100.6 MHz, CDCl3) δ 171.2, 153.3, 152.0, 151.9, 150.7, 150.5, 144.4, 131.5, 129.7, 114.1, 93.9, 84.6, 83.9, 83.4, 79.4, 68.6, 65.9, 62.3, 60.5, 59.2, 37.0, 30.4, 28.6, 27.9, 27.6, 25.2, 21.2, 14.3; HRMS (ESI-TOF) m/z: [M+H]+ calcd for C37H57N6O9 729.4174; Found 729.4180.

Reference： [1]Chen, Qi; Liu, Chong; Shulyak, Tetyana S.; Schneller, Stewart W. [Tetrahedron, 2014, vol. 70, # 4, p. 892 - 900]

52
[ 29786-93-4 ]
[ 95715-87-0 ]
[ 133625-87-3 ]

Yield	Reaction Conditions	Operation in experiment
64%	Stage #1: n-butyllithium With triphenylphosphine hydrobromide In tetrahydrofuran; hexane at 0℃; for 1h; Stage #2: (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine In tetrahydrofuran; hexane at 0 - 20℃; for 12h;	1.1 Step 1. tert-Butyl (45)-2, 2-dimethyl-4-vinyl-1, 3-oxazolidine-3-carboxylate Step 1. tert-Butyl (45)-2, 2-dimethyl-4-vinyl-1, 3-oxazolidine-3-carboxylateTo a suspension of methyl triphenylphosphonium bromide (5.63 g, 15.8 mmol) intetrahydrofuran (140 mL) was added 2.5 M n-butyllithium in hexane (7.35 mL, 18.4mmol). The deep red solution was stirred at 0 °C for 1 h. Then a solution of tert-butyl (4R)-4-formyl-2,2-dimethyl- 1,3 -oxazolidine-3 -carboxylate (from Aldrich, 3.01 g, 13.1mmol) in tetrahydrofuran (7.3 mL) was added drop wise at 0 °C. The red solution was warmed to room temperature and stirred for 12 h. Hexanes was added to the reaction mixture in 4:1 (v/v) ratio. The suspension was filtered through Celite and the filtrate concentrated. The resultant residue was purified by flash chromatography (eluting with10% ethyl acetate in hexanes) to give the desired compound as colorless oil (1.92 g,64%).

Reference： [1]Current Patent Assignee: INCYTE CORP - WO2015/184305, 2015, A1 Location in patent: Page/Page column 34; 35

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P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 133625-87-3 ] {[proInfo.proName]}

Quality Control of [ 133625-87-3 ]

Related Doc. of [ 133625-87-3 ]

Product Details of [ 133625-87-3 ]

Calculated chemistry of [ 133625-87-3 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

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Application In Synthesis of [ 133625-87-3 ]

[ 133625-87-3 ] Synthesis Path-Upstream 1~2

[ 133625-87-3 ] Synthesis Path-Downstream 1~52

Related Functional Groups of [ 133625-87-3 ]

Alkenes

Amides

Related Parent Nucleus of [ 133625-87-3 ]

Oxazolidines

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[ 133625-87-3 ]

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[ 133625-87-3 ]