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

Base Information

Chemical Name:methyl 2,3-didehydro-2,3-dideoxy-5-O-(tert-butyldiphenylsilyl)-α-D-glycero-pentafuranoside
CAS No.:148693-34-9
Molecular Formula:C₂₂H₂₈O₃Si
Molecular Weight:368.548
Hs Code.:

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

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Chemical Property of methyl 2,3-didehydro-2,3-dideoxy-5-O-(tert-butyldiphenylsilyl)-α-D-glycero-pentafuranoside

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Technology Process of methyl 2,3-didehydro-2,3-dideoxy-5-O-(tert-butyldiphenylsilyl)-α-D-glycero-pentafuranoside

There total 3 articles about methyl 2,3-didehydro-2,3-dideoxy-5-O-(tert-butyldiphenylsilyl)-α-D-glycero-pentafuranoside 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: 36.0%

: 130087-24-0
methyl 5-O-tert-butyldiphenylsilyl-3-iodo-2,3-dideoxy-α-D-threo-pentofuranoside

: 5188-07-8
sodium thiomethoxide

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

: 148693-33-8
methyl 2,3-dideoxy-3-methylthio-5-O-(tert-butyldiphenylsilyl)-α-D-erythro-pentafuranoside

Guidance literature:: In ethanol; for 3h; Heating;
DOI:10.1007/BF00808508

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

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

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: 36 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