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[ CAS No. 60933-68-8 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 60933-68-8
Chemical Structure| 60933-68-8
Structure of 60933-68-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 60933-68-8 ]

CAS No. :60933-68-8 MDL No. :MFCD00047076
Formula : C26H28O5 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 420.50 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 60933-68-8 ]

Physicochemical Properties

Num. heavy atoms : 31
Num. arom. heavy atoms : 18
Fraction Csp3 : 0.31
Num. rotatable bonds : 10
Num. H-bond acceptors : 5.0
Num. H-bond donors : 1.0
Molar Refractivity : 117.42
TPSA : 57.15 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.33 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.55
Log Po/w (XLOGP3) : 3.57
Log Po/w (WLOGP) : 3.64
Log Po/w (MLOGP) : 2.36
Log Po/w (SILICOS-IT) : 4.28
Consensus Log Po/w : 3.48

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.47
Solubility : 0.0144 mg/ml ; 0.0000342 mol/l
Class : Moderately soluble
Log S (Ali) : -4.46
Solubility : 0.0147 mg/ml ; 0.000035 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -7.53
Solubility : 0.0000125 mg/ml ; 0.0000000297 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 4.73

Safety of [ 60933-68-8 ]

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

Application In Synthesis of [ 60933-68-8 ]

* 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.

  • Downstream synthetic route of [ 60933-68-8 ]

[ 60933-68-8 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 60933-68-8 ]
  • [ 2393-23-9 ]
  • (3S,4S,5S)-3,4-Bis-benzyloxy-5-hydroxy-1-(4-methoxy-benzyl)-pyrrolidin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With 4 A molecular sieve In benzene Heating;
  • 2
  • [ 60933-68-8 ]
  • [ 14233-53-5 ]
YieldReaction ConditionsOperation in experiment
99% With sodium tetrahydroborate In ethanol
  • 3
  • [ 60933-68-8 ]
  • [ 94898-52-9 ]
  • [ 94898-40-5 ]
YieldReaction ConditionsOperation in experiment
With (bis-(2-methoxyethyl)amino)sulfur trufluoride In dichloromethane at 0℃; for 0.5h; Yield given; Yields of byproduct given. Title compound not separated from byproducts;
  • 4
  • [ 60933-68-8 ]
  • [ 19493-09-5 ]
  • [ 102208-53-7 ]
YieldReaction ConditionsOperation in experiment
74% In tetrahydrofuran
  • 5
  • [ 60933-68-8 ]
  • [ 14233-64-8 ]
YieldReaction ConditionsOperation in experiment
95% With bromobenzene; potassium carbonate; triphenylphosphine In tetrahydrofuran for 6h; Heating;
75% With acetic anhydride In dimethyl sulfoxide at 20℃; for 15h;
With molecular sieve; pyridinium chlorochromate In dichloromethane
  • 6
  • [ 60933-68-8 ]
  • [ 106-99-0 ]
  • octa-1',7'-dien-3'-yl 2,3,5-tri-O-benzyl-β-D-arabinofuranoside [ No CAS ]
  • (Z)-octa-2',7'-dien-1'-yl 2,3,5-tri-O-benzyl-α-D-arabinofuranoside [ No CAS ]
  • (E)-octa-2',7'-dien-1'-yl 2,3,5-tri-O-benzyl-α-D-arabinofuranoside [ No CAS ]
  • [ 14233-64-8 ]
YieldReaction ConditionsOperation in experiment
75% With triphenylphosphine In toluene at 75℃; for 24h; Further byproducts given;
  • 7
  • [ 13411-42-2 ]
  • [ 60933-68-8 ]
  • [ 889665-24-1 ]
  • 8
  • [ 60933-68-8 ]
  • [ 620946-66-9 ]
YieldReaction ConditionsOperation in experiment
With hydroxylamine hydrochloride; sodium methylate In methanol at 20℃; for 5h;
  • 10
  • [ 60933-68-8 ]
  • [ 123-54-6 ]
  • [ 1262899-98-8 ]
YieldReaction ConditionsOperation in experiment
54% Stage #1: acetylacetone With iron (III) chloride hexahydrate In 1,4-dioxane for 4h; Stage #2: 3,4,6-tri-O-benzyl-β-D-arabinofuranoside In 1,4-dioxane at 80℃; for 8h;
  • 11
  • [ 89824-86-2 ]
  • [ 60933-68-8 ]
  • [ 73068-66-3 ]
YieldReaction ConditionsOperation in experiment
With trifluoroacetic acid In water monomer; acetonitrile Inert atmosphere; optical yield given as %de;
With water monomer; acetic acid at 115℃; for 48h; Overall yield = 64 %; Overall yield = 4.8 g;
33.333 % de With sulfuric acid; acetic acid at 100℃; for 1h; Overall yield = 68 percent; Overall yield = 4.0 g; diastereoselective reaction; 2,3,5-Tri-O-benzyl-L-arabinofuranose (S3) To a solution of acetic acid (82 mL) and sulphuricacid (3 M aq., 22 mL) was added S2 (6.0 g, 14 mmol). The mixture was heated at 100 °C for 1 hand then it was cooled to r.t. The residue was neutralized with saturated aqueous K2CO3 and thenextracted twice with CH2Cl2. The combined organic layers were washed with water and brine,dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The product was purified by chromatography column on silica gel (EtOAc:Cyclohexane, 1:10→1:8 ) to obtain S3(4.0 g, 9.5 mmol, 68%, α:β= 2:1) as a white solid.
33.333 % de With sulfuric acid; acetic acid at 100℃; for 1h; Overall yield = 68 percent; Overall yield = 4.0 g; diastereoselective reaction; 2,3,5-Tri-O-benzyl-L-arabinofuranose (S3) To a solution of acetic acid (82 mL) and sulphuricacid (3 M aq., 22 mL) was added S2 (6.0 g, 14 mmol). The mixture was heated at 100 °C for 1 hand then it was cooled to r.t. The residue was neutralized with saturated aqueous K2CO3 and thenextracted twice with CH2Cl2. The combined organic layers were washed with water and brine,dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The product was purified by chromatography column on silica gel (EtOAc:Cyclohexane, 1:10→1:8 ) to obtain S3(4.0 g, 9.5 mmol, 68%, α:β= 2:1) as a white solid.

  • 12
  • [ 60933-68-8 ]
  • [ 545-06-2 ]
  • C28H28Cl3NO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane 3 To a stirring solution of 2,3,5-tri-O-benzyl-β-D-arabinofuranoside (250 mg, 0.594 mmol) in CH2Cl2 (0.05 M) were added trichloroacetonitrile (298 μL, 2.97 mmol) and DBU (44 μL, concentrated in vacuo and the residue was purified by flash column chromatography (15% EtOAc/hexanes, Rf=0.3). The intermediate imidate was isolated as an oil (261 mg, 78%). 1H-NMR (CDCl3, 400 MHz): δ 7.40-7.20 (m, 15H), 6.36 (s, 1H), 4.69 (d, J=11.9 Hz, 1H), 4.62-4.53 (m, 4H), 4.50 (d, J=2.0 Hz, 2H), 4.45 (q, J=5.1 Hz, 1H), 4.26 (d, J=2 Hz, 1H), 4.06 (dd, J=5.6, 2.0 Hz, 1H), 3.67 (d, J=4.9 Hz, 1H).
  • 13
  • C40H40O6 [ No CAS ]
  • [ 60933-68-8 ]
  • C40H40O7 [ No CAS ]
  • [ 123-08-0 ]
  • [ 73068-66-3 ]
YieldReaction ConditionsOperation in experiment
1: 40 % de 2: 51% 3: 16% With bis-[(trifluoroacetoxy)iodo]benzene In water; acetonitrile at 0℃; for 0.666667h; Synthesis of quinol 12 To a solution of phenol 11 (31.8 mg, 0.0516 mmol) in MeCN/H2O (8/1, 1.8 mL) was added PhI(OCOCF3)2(26.3 mg, 0.0612 mmol) at 0 °C. After stirring for 40 min, the reaction was quenched by adding saturatedaqueous NaHCO3 and 10% aqueous Na2S2O3. The mixture was extracted with EtOAc (×3). The combinedorganic extracts were washed with brine, dried (Na2SO4), and concentrated in vacuo. The residue was purifiedby PTLC (toluene/EtOAc = 8/2) to afford quinol 12 (5.3 mg, 16%) as a colorless oil and lactol 10 (8.3 mg,38%, α/β = 7/3) as a white solid along with some mixed fractions including lactol 10 and aldehyde 13.Further purification by PTLC (toluene/acetone = 8/2) gave an additional product of lactol 10 (6.6 mg, 30%,α/β = 7/3; total: 69%, α/β = 7/3) as a white solid and aldehyde 13 (3.2 mg, 51%) as a white solid.
  • 14
  • [ 115130-41-1 ]
  • [ 60933-68-8 ]
  • C42H44O9 [ No CAS ]
  • [ 73068-66-3 ]
YieldReaction ConditionsOperation in experiment
1: 40 % de 2: 1% With bis-[(trifluoroacetoxy)iodo]benzene In water; acetonitrile at 0℃; for 1.5h; Synthesis of quinol 9 and lactol 10 To a solution of phenol 5 (26.8 mg, 0.0396 mmol) in MeCN/H2O (3/1, 0.4 mL) was added PhI(OCOCF3)2(21.6 mg, 0.0502 mmol) at 0 °C. After stirring for 1.5 h, the reaction was quenched by adding saturatedaqueous NaHCO3 and 10% aqueous Na2S2O3. The mixture was extracted with EtOAc (×3). The combinedorganic extracts were washed with brine, dried (Na2SO4), and concentrated in vacuo. The residue was purifiedby PTLC (hexane/EtOAc = 5/5) to afford quinol 9 (0.4 mg, 1%) as a colorless oil, along with some mixedfractions including lactol 10. Further purification by PTLC (hexane/acetone = 7/3) gave lactol 10 (7.4 mg,44%, α/β = 7/3) as a white solid.
  • 15
  • [ 60933-68-8 ]
  • [ 196929-78-9 ]
  • 2,3,5-tri-O-benzyl-(RS)-N-tert-butanesulfinyl-β-D-arabinofuranosylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With titanium(IV) tetraethanolate In toluene at 110℃; for 1.5h; Molecular sieve; General procedure: A single-necked flask equipped with a reflux condenser and an argon inlet system was charged with related tri-O-benzyl-pentofuranose, 4 Å activated molecular sieves (0.4 g per mmol of substrate) and(S)- or (R)-2-methyl-2-propanesulfinamide (2.0 equiv.). Dry toluene (4 mL per mmol of substrate) was inserted and the mixture was stirred for 5 min at room temperature (~20 °C). Titanium(IV) ethoxide (Ti(OEt)4, 1.5 equiv.) was then added and the reaction mixture was stirred at 110 °C until no more starting material was observed by TLC (generally,1.5 h). The content was next allowed to reach 20 °C and NaBH4 (4.0 equiv.) was added. The resulting suspension was stirred at 110 °C until no more sulfinyl glycosylamine intermediate remained in the reaction mixture (1 h). The suspension was then allowed to cool down to room temperature and sat. aqueous NaCl was added. The mixture was stirred at 20 °C for 10 min and the precipitate and molecular sieves were filtered through a pad of Celite. The cake was rinsed (EtOAc) and the aqueous layer was discarded. The organic phase was washed (sat. aq.NH4Cl), dried over MgSO4, filtered through a cotton plug and concentrated in vacuo. The crude product was purified through column chromatography (SiO2, PE:EtOAc) to provide the 1-N-tert-butanesulfinylamino-1-deoxy-pentitol derivative.
  • 16
  • [ 60933-68-8 ]
  • [ 224952-98-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere 2: C50H55F9N6O4S2 / 5 h / 40 °C / Molecular sieve; Inert atmosphere
  • 17
  • [ 60933-68-8 ]
  • (2R,3R,4S,5R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-isopropoxytetrahydrofuran [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere 2: C50H55F9N6O4S2 / 5 h / 40 °C / Molecular sieve; Inert atmosphere
  • 18
  • [ 60933-68-8 ]
  • (2R,3R,4S,5R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-isopropoxytetrahydrofuran [ No CAS ]
  • (2R,3R,4S,5S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-isopropoxy-tetrahydro-furan [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere 2: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -78 °C / Inert atmosphere
  • 19
  • [ 60933-68-8 ]
  • (3aR,5R,5aS,8aS,8bR)-5-((((2R,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)oxy)methyl)-2,2,7,7-tetramethyltetrahydro-5H-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere 2: C50H55F9N6O4S2 / 3 h / 40 °C / Molecular sieve; Inert atmosphere
  • 20
  • [ 60933-68-8 ]
  • (3aR,5R,5aS,8aS,8bR)-5-((((2R,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)oxy)methyl)-2,2,7,7-tetramethyltetrahydro-5H-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran [ No CAS ]
  • C38H46O10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere 2: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -78 °C / Inert atmosphere
  • 21
  • [ 60933-68-8 ]
  • (((3aS,4R,6S,7R,7aS)-7-(((2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)oxy)-6-methoxy-2,2-dimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-4-yl)methoxy)(tert-butyl)diphenylsilane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere 2: C50H55F9N6O4S2 / 18 h / 40 °C / Molecular sieve; Inert atmosphere
  • 22
  • [ 60933-68-8 ]
  • (((3aS,4R,6S,7R,7aS)-7-(((2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)oxy)-6-methoxy-2,2-dimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-4-yl)methoxy)(tert-butyl)diphenylsilane [ No CAS ]
  • C52H62O10Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere 2: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -78 °C / Inert atmosphere
  • 23
  • [ 60933-68-8 ]
  • (3aR,4S,6R,7S,7aR)-7-(((2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)oxy)-6-methoxy-2,2,4-trimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere 2: C50H55F9N6O4S2 / 18 h / 40 °C / Molecular sieve; Inert atmosphere
  • 24
  • [ 60933-68-8 ]
  • (3aR,4S,6R,7S,7aR)-7-(((2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)oxy)-6-methoxy-2,2,4-trimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran [ No CAS ]
  • C36H44O9 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere 2: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -78 °C / Inert atmosphere
  • 25
  • [ 60933-68-8 ]
  • (3aR,4R,6S,7S,7aR)-7-(((2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)oxy)-4-methoxy-2,2,6-trimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere 2: C50H55F9N6O4S2 / 18 h / 40 °C / Molecular sieve; Inert atmosphere
  • 26
  • [ 60933-68-8 ]
  • (3aR,4R,6S,7S,7aR)-7-(((2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)oxy)-4-methoxy-2,2,6-trimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran [ No CAS ]
  • C36H44O9 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere 2: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -78 °C / Inert atmosphere
  • 27
  • [ 60933-68-8 ]
  • (4aR,6S,7R,8S,8aR)-8-(benzyloxy)-7-(((2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)oxy)-6-methoxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere 2: C50H55F9N6O4S2 / 48 h / 40 °C / Molecular sieve; Inert atmosphere
  • 28
  • [ 60933-68-8 ]
  • (4aR,6S,7R,8S,8aR)-8-(benzyloxy)-7-(((2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)oxy)-6-methoxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxine [ No CAS ]
  • C47H50O10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere 2: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -78 °C / Inert atmosphere
  • 29
  • [ 60933-68-8 ]
  • (2S,3R,4S,5R,6R)-3,4-bis(allyloxy)-6-((benzyloxy)methyl)-5-(((2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)oxy)-2-methoxytetrahydro-2H-pyran [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere 2: C50H55F9N6O4S2 / 48 h / 40 °C / Molecular sieve; Inert atmosphere
  • 30
  • [ 60933-68-8 ]
  • (2R,3R,4S,5R)-3,4-bis(benzyloxy)-5-(((2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)oxy)-2-methoxytetrahydro-2H-pyran [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere 2: C50H55F9N6O4S2 / 48 h / 40 °C / Molecular sieve; Inert atmosphere
  • 31
  • [ 60933-68-8 ]
  • (2R,3R,4S,5R)-3,4-bis(benzyloxy)-5-(((2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)oxy)-2-methoxytetrahydro-2H-pyran [ No CAS ]
  • C46H50O9 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere 2: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -78 °C / Inert atmosphere
  • 32
  • [ 60933-68-8 ]
  • (2R,3R,4S,5R)-4,5-bis(benzyloxy)-3-(((2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)oxy)-2-methoxytetrahydro-2H-pyran [ No CAS ]
  • C46H50O9 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere 2: C50H55F9N6O4S2 / 48 h / 40 °C / Molecular sieve; Inert atmosphere
  • 33
  • [ 60933-68-8 ]
  • (2S,3S,4R,5R)-3,4-bis(benzyloxy)-2-(((2S,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-methoxytetrahydrofuran-3-yl)oxy)-5-((benzyloxy)methyl)tetrahydrofuran [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere 2: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -78 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere 2: C50H55F9N6O4S2 / 18 h / 40 °C / Molecular sieve; Inert atmosphere
  • 34
  • [ 60933-68-8 ]
  • (2S,3S,4R,5R)-3,4-bis(benzyloxy)-2-(((2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-methoxytetrahydrofuran-3-yl)oxy)-5-((benzyloxy)methyl)tetrahydrofuran [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere 2: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -78 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere 2: C50H55F9N6O4S2 / 18 h / 40 °C / Molecular sieve; Inert atmosphere
  • 35
  • [ 60933-68-8 ]
  • (3a'R,5'R,6'S,6a'R)-6'-(((2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)oxy)-5'-((R)-1,4-dioxaspiro[4.5]decan-2-yl)tetrahydrospiro[cyclohexane-1,2'-furo[2,3-d][1,3]dioxole] [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere 2: C50H55F9N6O4S2 / 48 h / 40 °C / Molecular sieve; Inert atmosphere
  • 36
  • [ 60933-68-8 ]
  • (3a'R,5'R,6'S,6a'R)-6'-(((2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)oxy)-5'-((R)-1,4-dioxaspiro[4.5]decan-2-yl)tetrahydrospiro[cyclohexane-1,2'-furo[2,3-d][1,3]dioxole] [ No CAS ]
  • C44H54O10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere 2: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -78 °C / Inert atmosphere
  • 37
  • [ 60933-68-8 ]
  • [ 402758-89-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere 2: C50H55F9N6O4S2 / 48 h / 40 °C / Molecular sieve; Inert atmosphere
  • 38
  • [ 60933-68-8 ]
  • methyl (2,3,5-tri-O-benzyl-α-D-arabinofuranosyl)-(1->2)-3,5-di-O-benzyl-α-D-arabinofuranoside [ No CAS ]
  • [ 402758-89-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere 2: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -78 °C / Inert atmosphere
  • 39
  • [ 60933-68-8 ]
  • methyl O-((2R,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)-N-(tert-butoxycarbonyl)-L-threoninate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere 2: C50H55F9N6O4S2 / 18 h / 40 °C / Molecular sieve; Inert atmosphere
  • 40
  • [ 60933-68-8 ]
  • methyl O-((2R,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)-N-(tert-butoxycarbonyl)-L-threoninate [ No CAS ]
  • C36H45NO9 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere 2: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -78 °C / Inert atmosphere
  • 41
  • [ 60933-68-8 ]
  • methyl O-((2R,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)-N-(tert-butoxycarbonyl)-D-threoninate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere 2: C50H55F9N6O4S2 / 18 h / 40 °C / Molecular sieve; Inert atmosphere
  • 42
  • [ 60933-68-8 ]
  • methyl O-((2R,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)-N-(tert-butoxycarbonyl)-D-threoninate [ No CAS ]
  • C36H45NO9 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere 2: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -78 °C / Inert atmosphere
  • 43
  • [ 60933-68-8 ]
  • methyl O-((2R,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)-N-(tert-butoxycarbonyl)-L-serinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere 2: C50H55F9N6O4S2 / 18 h / 40 °C / Molecular sieve; Inert atmosphere
  • 44
  • [ 60933-68-8 ]
  • methyl O-((2R,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)-N-(tert-butoxycarbonyl)-L-serinate [ No CAS ]
  • C35H43NO9 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere 2: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -78 °C / Inert atmosphere
  • 45
  • [ 60933-68-8 ]
  • 1-(tert-butyl) 2-methyl (2S,4R)-4-(((2R,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)oxy)pyrrolidine-1,2-dicarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere 2: C50H55F9N6O4S2 / 18 h / 40 °C / Molecular sieve; Inert atmosphere
  • 46
  • [ 60933-68-8 ]
  • 1-(tert-butyl) 2-methyl (2S,4R)-4-(((2R,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)oxy)pyrrolidine-1,2-dicarboxylate [ No CAS ]
  • C37H45NO9 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere 2: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -78 °C / Inert atmosphere
  • 47
  • [ 60933-68-8 ]
  • Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yloxymethyl)-6-methoxy-tetrahydro-pyran-4-yl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere 2: 18 h / 40 °C / Molecular sieve; Inert atmosphere
  • 48
  • [ 60933-68-8 ]
  • C39H46O13 [ No CAS ]
  • Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yloxymethyl)-6-methoxy-tetrahydro-pyran-4-yl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere 2: C50H55F9N6O4S2 / 18 h / 40 °C / Molecular sieve; Inert atmosphere
  • 49
  • [ 4090-55-5 ]
  • [ 60933-68-8 ]
  • 2-(((2R,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)oxy)-5,5-dimethyl-1,3,2-dioxaphosphinane 2-oxide [ No CAS ]
  • 50
  • [ 60933-68-8 ]
  • [ 58479-61-1 ]
  • (1Z)-2,3,5-tri-O-benzyl-4-deoxy-4-iodo-L-xylose O-[(tert-butyl)triphenylsilyl]oxime [ No CAS ]
  • [ 631915-22-5 ]
YieldReaction ConditionsOperation in experiment
73% Stage #1: 3,4,6-tri-O-benzyl-β-D-arabinofuranoside With methanol; hydroxylamine hydrochloride; sodium In hexane; water at 20℃; for 2h; Inert atmosphere; Stage #2: tert-butylchlorodiphenylsilane With 1H-imidazole In dichloromethane at 20℃; for 0.5h; Inert atmosphere; Overall yield = 73 percent; Overall yield = 9.69 g; Further stages;
Same Skeleton Products
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