Methyl 5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-3-C-methylene-β-D-glycero-pentofuranoside

Base Information

Chemical Name:Methyl 5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-3-C-methylene-β-D-glycero-pentofuranoside
CAS No.:172342-54-0
Molecular Formula:C₂₃H₃₀O₃Si
Molecular Weight:382.575
Hs Code.:

Synonyms:Methyl 5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-3-C-methylene-β-D-glycero-pentofuranoside

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Chemical Property of Methyl 5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-3-C-methylene-β-D-glycero-pentofuranoside

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Technology Process of Methyl 5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-3-C-methylene-β-D-glycero-pentofuranoside

There total 4 articles about Methyl 5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-3-C-methylene-β-D-glycero-pentofuranoside 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: 60.0%

: 172342-52-8
Methyl 5-O-(tert-butyldiphenylsilyl)-2-deoxy-β-D-glycero-pentofuranosid-3-ulose

: 74-95-3
1,1-dibromomethane

: 172342-54-0
Methyl 5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-3-C-methylene-β-D-glycero-pentofuranoside

Guidance literature:: With titanium tetrachloride; zinc; In tetrahydrofuran; dichloromethane; 1.) 0 deg C, 15 min, 2.) r.t., 45 min;
DOI:10.1021/jo00127a041

Reference yield:

: 130144-86-4
(2R,3S,5R)-2-tert-butyldiphenylsilanyloxymethyl-3-hydroxy-5β-methoxytetrahydrofuran

: 172342-54-0
Methyl 5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-3-C-methylene-β-D-glycero-pentofuranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 89 percent / pyridine, CrO₃, Ac₂O / CH₂Cl₂ / 0.25 h / Ambient temperature

2: 60 percent / Zn, TiCl₄ / CH₂Cl₂; tetrahydrofuran / 1.) 0 deg C, 15 min, 2.) r.t., 45 min

With pyridine; chromium(VI) oxide; acetic anhydride; titanium tetrachloride; zinc; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo00127a041

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 172342-54-0
Methyl 5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-3-C-methylene-β-D-glycero-pentofuranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 26 percent / imidazole / dimethylformamide

2: 89 percent / pyridine, CrO₃, Ac₂O / CH₂Cl₂ / 0.25 h / Ambient temperature

3: 60 percent / Zn, TiCl₄ / CH₂Cl₂; tetrahydrofuran / 1.) 0 deg C, 15 min, 2.) r.t., 45 min

With pyridine; 1H-imidazole; chromium(VI) oxide; acetic anhydride; titanium tetrachloride; zinc; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00127a041