[ CAS No. 1607-37-0 ] {[proInfo.proName]}

Name: 1607-37-0|4-[(2,3-Epoxypropoxy)methyl]-2,2-dimethyl-1,3-dioxolane|95%
Brand: Ambeed
SKU: A411107
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COA NMR CNMR HPLC LC-MS

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Product Details of [ 1607-37-0 ]

CAS No. :	1607-37-0	MDL No. :	MFCD07370127
Formula :	C₉H₁₆O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DOUYENKDWOPECR-UHFFFAOYSA-N
M.W :	188.22	Pubchem ID :	10921278
Synonyms :

Safety of [ 1607-37-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P305+P351+P338	UN#:	N/A
Hazard Statements:	H227-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1607-37-0 ]

* 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 [ 1607-37-0 ]
Downstream synthetic route of [ 1607-37-0 ]

[ 1607-37-0 ] Synthesis Path-Upstream 1~2

1
[ 1607-37-0 ]
[ 107-19-7 ]
[ 18180-30-8 ]

Reference： [1] Tetrahedron, 1996, vol. 52, # 18, p. 6437 - 6452

2
[ 106-89-8 ]
[ 100-79-8 ]
[ 1607-37-0 ]

Yield	Reaction Conditions	Operation in experiment
29%	With tetrabutylammomium bromide; sodium hydroxide In benzene at 0℃; for 48 h;	2.2.1.4 Synthesis of 1,2-isopropylidene glyceryl glycidyl ether (3b) A mixture of solketal 3a (98 mmol), epichlorohydrine (198 mmol), benzene (20 mL), 50percent NaOH (20 mL) and tetra-n-butylammonium bromide (TBAB, 10 mmol) was cooled down to 0 °C and then stirred for 48 h. The reaction mixture was diluted with diethyl ether and washed with water (3 * 75 mL), saturated NaHCO₃ solution (3 * 75 mL) and brine (3 * 75 mL). The collected organic phase was dried over Na₂SO₄, filtered and evaporated under reduced pressure. Afterwards, the product was distilled at 165 °C and 1.2 mbar (b.p. 90 °C). 3b was obtained as a colorless liquid. Yield: 29percent. ¹H NMR (500 MHz, CDCl₃): δ 1.34 (m, 3H, CH₃), 1.40 (m, 3H, CH₃), 2.58 (ddd, J = 5.0, 3.9, 2.7 Hz, 1H, H-7), 2.73-2.82 (m, 1H, H-7), 3.08-3.18 (m, 1H), 3.40 (ddd, J = 17.6, 11.7, 6.0 Hz, 1H), 3.46-3.64 (m, 2H), 3.71 (td, J = 8,3, 6.4 Hz, 1H), 3.80 (ddd, J = 13.4, 11.7, 2.9 Hz, 1H), 4.04 (ddd, J = 8.0, 6.4, 1.5 Hz, 1H), 4.27 (dq, J = 11.6, 5.8, 5.3 Hz, 1H, H-1) ppm. ¹H NMR data are in agreement with data reported in the literature

Reference： [1] Macromolecules, 2010, vol. 43, # 13, p. 5582 - 5588
[2] Inorganica Chimica Acta, 2016, vol. 452, p. 159 - 169
[3] Tetrahedron, 1996, vol. 52, # 18, p. 6437 - 6452
[4] Patent: US4927941, 1990, A,
[5] Patent: US4977273, 1990, A,

[ 1607-37-0 ] Synthesis Path-Downstream 1~13

1
[ 1607-37-0 ]
[ 107-19-7 ]
[ 18180-30-8 ]

Reference： [1]Tetrahedron,1996,vol. 52,p. 6437 - 6452

2
[ 1607-37-0 ]
[ 107-19-7 ]
4-<(2-hydroxy-3-propynyloxy)propyloxymethyl>-2,2-dimethyl-1,3-dioxalane [ No CAS ]

Reference： [1]Tetrahedron,1996,vol. 52,p. 6437 - 6452

3
[ 106-89-8 ]
[ 100-79-8 ]
[ 1607-37-0 ]

Yield	Reaction Conditions	Operation in experiment
29%	With tetrabutylammomium bromide; sodium hydroxide; In benzene; at 0℃; for 48.0h;	2.2.1.4 Synthesis of 1,2-isopropylidene glyceryl glycidyl ether (3b) A mixture of solketal 3a (98 mmol), epichlorohydrine (198 mmol), benzene (20 mL), 50% NaOH (20 mL) and tetra-n-butylammonium bromide (TBAB, 10 mmol) was cooled down to 0 C and then stirred for 48 h. The reaction mixture was diluted with diethyl ether and washed with water (3 * 75 mL), saturated NaHCO3 solution (3 * 75 mL) and brine (3 * 75 mL). The collected organic phase was dried over Na2SO4, filtered and evaporated under reduced pressure. Afterwards, the product was distilled at 165 C and 1.2 mbar (b.p. 90 C). 3b was obtained as a colorless liquid. Yield: 29%. 1H NMR (500 MHz, CDCl3): delta 1.34 (m, 3H, CH3), 1.40 (m, 3H, CH3), 2.58 (ddd, J = 5.0, 3.9, 2.7 Hz, 1H, H-7), 2.73-2.82 (m, 1H, H-7), 3.08-3.18 (m, 1H), 3.40 (ddd, J = 17.6, 11.7, 6.0 Hz, 1H), 3.46-3.64 (m, 2H), 3.71 (td, J = 8,3, 6.4 Hz, 1H), 3.80 (ddd, J = 13.4, 11.7, 2.9 Hz, 1H), 4.04 (ddd, J = 8.0, 6.4, 1.5 Hz, 1H), 4.27 (dq, J = 11.6, 5.8, 5.3 Hz, 1H, H-1) ppm. 1H NMR data are in agreement with data reported in the literature
	With potassium hydroxide; In 1,4-dioxane;	PREPARATION EXAMPLE 39 STR22 To a solution of 6.0 g (50 mmol) of 1,2-O-isopropylideneglycerol and 18.5 g (0.2 mmol) of epichlorohydrin in 50 ml of dioxane, 2.8 g (50 mmol) of potassium hydroxide was added and reacted for 3 hours at 70 C. After the reaction, the reaction mixture was filtered and the filtrate was concentrated to give 6.9 g of 3-(2,3-epoxypropyl)-1,2-O-isopropylideneglycerol.
	With potassium carbonate; In 1,4-dioxane;	PREPARATION EXAMPLE 1 STR9 To a solution of 1,2-O-isopropylideneglycerol (6.0 g, 50 mmol) and epichlorohydrin (18.5 g, 0.2 mol) in dioxane (50 ml), potassium carbonate (2.8 g, 50 mmol) was added and stirred for 3 hours at 70 C. The reaction mixture was filtered and the filtrate was concentrated to obtain 3-O-(2,3-epoxypropyl)-1,2-O-isopropylideneglycerol (6.9 g).

Reference： [1]Macromolecules,2010,vol. 43,p. 5582 - 5588
[2]Inorganica Chimica Acta,2016,vol. 452,p. 159 - 169
[3]Tetrahedron,1996,vol. 52,p. 6437 - 6452
[4]Patent: US4927941,1990,A
[5]Patent: US4977273,1990,A

5
[ 220756-50-3 ]
[ 1607-37-0 ]
C₃₈H₇₄NO₁₀P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In tetrahydrofuran; water; for 2.0h;Heating / reflux;	B) Preparation of erucoyl-1,3-propanediol-phospho-N,N-dimethyl-N-(hydroxypropyldihydroxypropyl)-propylammoniumExample 155 This compound can be prepared by using the intermediate erucoyl-1,3-propanediol-phospho-N-methylpropylammonium. It is converted in a reaction firstly with an epoxide and immediately further methylated to give the final product. Erucoyl-1,3-propanediol-phospho-N-methylpropylammonium, 54.8 g (MW 547.8; 0.1 mol) is mixed with 800 ml of THF and 83 g of K2CO3 (0.6 mol) in 800 ml of H2O and heated to 500 C. to result in a two phase solution. While stirring vigorously, a solution of 21 g of 1,2-isopropylideneglycero-3,1-glycidol (MW 188.2; 0.11 mol) in 200 ml of THF is added dropwise, and the temperature is raised to 600 C. The reaction mixture is boiled under gentle reflux for 2 hours,

Reference： [1]Patent: US6344576,2002,B1 .Location in patent: Page column 8

6
[ 1607-37-0 ]
[ 13925-12-7 ]
C₂₂H₂₆N₂O₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 18-crown-6 ether; potassium carbonate; In N,N-dimethyl-formamide; at 0 - 20℃;	General procedure: lodinin from Example 4c (1 mmol), K2C03 (1-10 mmol) and 18-crown-6-ether (1-2 mmol) were dispersed in anhydrous DMF (10 mL). The resulting mixture was cooled down to 0C and alkylating agent (1.25 eq for monoalkylation of iodinin or myxin, 2.5 equivalents for dialkylation of iodinin) added and the reaction mixture left stirring overnight gradually reaching ambient temperature. The reaction mixture was diluted by H20 (250 mL) and extracted with EtOAc (4x 50 mL). The organic phases were pooled and washed with brine (4x 1 OOmL) and dried over MgSO4 and filtered before solvents were removed under reduced pressure. The resulting crude compound was dry loaded on silica and further purified by flash column chromatography on silica (10-50% EtOAc as the eluent) to yield mono-or dialkylated iodinin or alkylated myxin.:_Myxin from Example 6 was alkylated following the general procedure in Example 5. The acetonide was cleaved as described in Lewbart et al, J. Org. Chem. 34 (1969) 3505. The resulting solution was evaporated to dryness. The resulting crude compound was dry loaded on silica and further purified by flash column chromatography on silica (10-50% H20/EtOAc as the eluent) affording a red solid.

Reference： [1]Patent: WO2015/63516,2015,A2 .Location in patent: Page/Page column 23; 24; 25

7
[ 1607-37-0 ]
1,2-isopropylidene glyceryl (1-azido-2-propanol) ether [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With sodium azide; ammonium chloride; In ethanol; at 100℃; for 18.0h;Reflux;	A mixture of 3b (29 mmol), sodium azide (144 mmol) and ammonium chloride (66 mmol) in 80% EtOH (150 mL) was refluxed at 100 C for 18 h. The reaction mixture was poured into ice-cold water. The solution was extracted with dichloromethane and washed with water (3 * 50 mL) and brine (3 * 50 mL). The organic phase was dried over Na2SO4, filtered and evaporated under reduced pressure. 3c was obtained as a light yellow oil. Yield: 85%. 1H NMR (500 MHz, CDCl3): delta 1.33 (m, 3H, CH3), 1.40 (m, 3H, CH3), 2.92 (dd, J = 7.8, 4.9 Hz, 1H), 3.26-3.40 (m, 2H), 3.47-3.61 (m, 4H), 3.69 (ddd, J = 8.3, 6.4, 2.9 Hz, 1H), 3.88-3.97 (m, 1H), 3.99-4.06 (m, 1H), 4.21-4.31 (m, 1H, H-1) ppm; 13C NMR (126 MHz, CDCl3): delta 25.4 (CH3), 26.8 (CH3), 53.4 (2x), 66.4 (2x), 69.7 (2x), 72.6 (2x), 73.0 (2x), 74.8 (2x), 109.7 ppm. Both 1H NMR and 13C NMR data are in agreement with data reported in the literature