α-5-O-tert-butyldiphenylsilyl-D-2,3-dideoxy-2,3-endo-methylenepentofuranosyl chloride

Base Information

Chemical Name:α-5-O-tert-butyldiphenylsilyl-D-2,3-dideoxy-2,3-endo-methylenepentofuranosyl chloride
CAS No.:201853-29-4
Molecular Formula:C₂₂H₂₇ClO₂Si
Molecular Weight:386.994
Hs Code.:

Synonyms:α-5-O-tert-butyldiphenylsilyl-D-2,3-dideoxy-2,3-endo-methylenepentofuranosyl chloride

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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 α-5-O-tert-butyldiphenylsilyl-D-2,3-dideoxy-2,3-endo-methylenepentofuranosyl chloride

Chemical Property:

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Technology Process of α-5-O-tert-butyldiphenylsilyl-D-2,3-dideoxy-2,3-endo-methylenepentofuranosyl chloride

There total 7 articles about α-5-O-tert-butyldiphenylsilyl-D-2,3-dideoxy-2,3-endo-methylenepentofuranosyl chloride 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:

: α/β-5-O-tert-butyldiphenylsilyl-D-2,3-dideoxy-2,3-endo-methylenepentofuranose

: 201853-29-4
α-5-O-tert-butyldiphenylsilyl-D-2,3-dideoxy-2,3-endo-methylenepentofuranosyl chloride

Guidance literature:: With tetrachloromethane; triphenylphosphine; In tetrahydrofuran; at 50 ℃; for 3h;
DOI:10.1021/jo991212l

Reference yield:

: 201853-28-3
α/β-5-O-tert-butyldiphenylsilyl-D-2,3-dideoxy-2,3-endo-methylenepentofuranosyl acetate

: 201853-29-4
α-5-O-tert-butyldiphenylsilyl-D-2,3-dideoxy-2,3-endo-methylenepentofuranosyl chloride

Guidance literature:: With hydrogenchloride; In diethyl ether; at -10 ℃; for 0.0833333h;
DOI:10.1016/S0040-4039(97)10531-7

Reference yield:

: 153861-49-5
(1R,2S,4'S)-1-(2',2'-dimethyl-1',3'-dioxolane-4'-yl)-2-(hydroxymethyl)cyclopropane

: 201853-29-4
α-5-O-tert-butyldiphenylsilyl-D-2,3-dideoxy-2,3-endo-methylenepentofuranosyl chloride

Guidance literature:: Multi-step reaction with 5 steps

1: DMSO; oxalic chloride; Et₃N / CH₂Cl₂ / 0.25 h / -78 °C

2: 0.1 N HCl / dioxane / 4 h / 20 °C

3: pyridine / CH₂Cl₂ / 24 h / 0 - 20 °C

4: 87 percent / pyridine / 0.5 h

5: HCl / diethyl ether / 0.17 h / -10 °C

With pyridine; hydrogenchloride; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In 1,4-dioxane; pyridine; diethyl ether; dichloromethane; 1: Oxidation / 2: Cyclization / 3: silylation / 4: Acetylation / 5: Substitution;
DOI:10.1021/jo991212l