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

Base Information

Chemical Name:(2R,3R,5S)-2-tert-butyldiphenylsilyloxymethyl-3-chloro-5-methoxy-tetrahydrofuran
CAS No.:444804-72-2
Molecular Formula:C₂₂H₂₉ClO₃Si
Molecular Weight:405.009
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2R,3R,5S)-2-tert-butyldiphenylsilyloxymethyl-3-chloro-5-methoxy-tetrahydrofuran

Chemical Property:

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Technology Process of (2R,3R,5S)-2-tert-butyldiphenylsilyloxymethyl-3-chloro-5-methoxy-tetrahydrofuran

There total 2 articles about (2R,3R,5S)-2-tert-butyldiphenylsilyloxymethyl-3-chloro-5-methoxy-tetrahydrofuran 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: 62.0%

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

: 148693-34-9
methyl 2,3-didehydro-2,3-dideoxy-5-O-(tert-butyldiphenylsilyl)-α-D-glycero-pentafuranoside

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

Guidance literature:: With pyridine; dichloromethylenedimethyliminium chloride; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1016/S0040-4020(02)00049-2

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

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

Guidance literature:: Multi-step reaction with 2 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

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

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