(3S,5R,6R)-7-tert-butyldiphenylsilyloxy-5-chloro-3,6-dihydroxy-hept-1-ene

Base Information

Chemical Name:(3S,5R,6R)-7-tert-butyldiphenylsilyloxy-5-chloro-3,6-dihydroxy-hept-1-ene
CAS No.:444804-77-7
Molecular Formula:C₂₃H₃₁ClO₃Si
Molecular Weight:419.036
Hs Code.:

Synonyms:(3S,5R,6R)-7-tert-butyldiphenylsilyloxy-5-chloro-3,6-dihydroxy-hept-1-ene

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Chemical Property of (3S,5R,6R)-7-tert-butyldiphenylsilyloxy-5-chloro-3,6-dihydroxy-hept-1-ene

Chemical Property:

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Technology Process of (3S,5R,6R)-7-tert-butyldiphenylsilyloxy-5-chloro-3,6-dihydroxy-hept-1-ene

There total 3 articles about (3S,5R,6R)-7-tert-butyldiphenylsilyloxy-5-chloro-3,6-dihydroxy-hept-1-ene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 1826-67-1
vinyl magnesium bromide

: 444804-72-2
(2R,3R,5S)-2-tert-butyldiphenylsilyloxymethyl-3-chloro-5-methoxy-tetrahydrofuran

: 444804-77-7
(3S,5R,6R)-7-tert-butyldiphenylsilyloxy-5-chloro-3,6-dihydroxy-hept-1-ene

: 444804-76-6
(3R,5R,6R)-7-tert-butyldiphenylsilyloxy-5-chloro-3,6-dihydroxy-hept-1-ene

Guidance literature:: (2R,3R,5S)-2-tert-butyldiphenylsilyloxymethyl-3-chloro-5-methoxy-tetrahydrofuran; With boron trichloride - methyl sulfide complex; In diethyl ether; dichloromethane; for 0.166667h;

vinyl magnesium bromide; In tetrahydrofuran; at 0 ℃; for 1.5h;
DOI:10.1016/S0040-4020(02)00049-2

Reference yield:

: 130144-85-3
(2R,3S,5S)-2-tert-butyldiphenylsilanyloxymethyl-3-hydroxy-5α-methoxytetrahydrofuran

: 444804-77-7
(3S,5R,6R)-7-tert-butyldiphenylsilyloxy-5-chloro-3,6-dihydroxy-hept-1-ene

Guidance literature:: Multi-step reaction with 2 steps

1.1: 62 percent / pyridine; (dichloromethylene)dimethyl-ammonium chloride / CH₂Cl₂ / 1 h / 20 °C

2.1: BCl₃*SMe₂ / diethyl ether; CH₂Cl₂ / 0.17 h

2.2: 183 mg / tetrahydrofuran / 1.5 h / 0 °C

With pyridine; boron trichloride - methyl sulfide complex; dichloromethylenedimethyliminium chloride; In diethyl ether; dichloromethane;
DOI:10.1016/S0040-4020(02)00049-2

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 444804-77-7
(3S,5R,6R)-7-tert-butyldiphenylsilyloxy-5-chloro-3,6-dihydroxy-hept-1-ene

Guidance literature:: Multi-step reaction with 3 steps

1.1: aq. HCl / diethyl ether / 0.5 h / 20 °C

1.2: 42 percent / pyridine / 18 h / 20 °C

2.1: 62 percent / pyridine; (dichloromethylene)dimethyl-ammonium chloride / CH₂Cl₂ / 1 h / 20 °C

3.1: BCl₃*SMe₂ / diethyl ether; CH₂Cl₂ / 0.17 h

3.2: 183 mg / tetrahydrofuran / 1.5 h / 0 °C

With pyridine; hydrogenchloride; boron trichloride - methyl sulfide complex; dichloromethylenedimethyliminium chloride; In diethyl ether; dichloromethane;
DOI:10.1016/S0040-4020(02)00049-2