isopropyl 3-O-benzyl-2-O-tert-butyldimethylsilyl-4,6-O-isopropylidene-5-C-vinyl-β-D-glucopyranoside

Base Information

Chemical Name:isopropyl 3-O-benzyl-2-O-tert-butyldimethylsilyl-4,6-O-isopropylidene-5-C-vinyl-β-D-glucopyranoside
CAS No.:753502-45-3
Molecular Formula:C₂₇H₄₄O₆Si
Molecular Weight:492.728
Hs Code.:

Synonyms:isopropyl 3-O-benzyl-2-O-tert-butyldimethylsilyl-4,6-O-isopropylidene-5-C-vinyl-β-D-glucopyranoside

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Chemical Property of isopropyl 3-O-benzyl-2-O-tert-butyldimethylsilyl-4,6-O-isopropylidene-5-C-vinyl-β-D-glucopyranoside

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Technology Process of isopropyl 3-O-benzyl-2-O-tert-butyldimethylsilyl-4,6-O-isopropylidene-5-C-vinyl-β-D-glucopyranoside

There total 4 articles about isopropyl 3-O-benzyl-2-O-tert-butyldimethylsilyl-4,6-O-isopropylidene-5-C-vinyl-β-D-glucopyranoside 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: 97.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 753502-54-4
(4aR,6R,7R,8R,8aS)-8-Benzyloxy-6-isopropoxy-2,2-dimethyl-4a-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

: 753502-45-3
isopropyl 3-O-benzyl-2-O-tert-butyldimethylsilyl-4,6-O-isopropylidene-5-C-vinyl-β-D-glucopyranoside

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 60 ℃; for 3.5h;
DOI:10.1016/j.tet.2004.06.009

Reference yield:

: 612841-73-3
1,2,4,6-tetra-O-acetyl-3-O-benzyl-5-C-vinyl-β-D-glucopyranoside

: 753502-45-3
isopropyl 3-O-benzyl-2-O-tert-butyldimethylsilyl-4,6-O-isopropylidene-5-C-vinyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 76 percent / 4 Angstroem molecular sieves; TMSOTf / CH₂Cl₂ / -78 - 20 °C

2: sodium; MeOH / 16 h / 20 °C

3: 86 percent / camphorsulfonic acid / acetone / 20 °C

4: 97 percent / imidazole / dimethylformamide / 3.5 h / 60 °C

With 1H-imidazole; methanol; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; camphor-10-sulfonic acid; sodium; In dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1016/j.tet.2004.06.009

Reference yield:

: 612841-85-7
isopropyl 2,4,6-tri-O-acetyl-3-O-benzyl-5-C-vinyl-β-D-glucopyranoside

: 753502-45-3
isopropyl 3-O-benzyl-2-O-tert-butyldimethylsilyl-4,6-O-isopropylidene-5-C-vinyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: sodium; MeOH / 16 h / 20 °C

2: 86 percent / camphorsulfonic acid / acetone / 20 °C

3: 97 percent / imidazole / dimethylformamide / 3.5 h / 60 °C

With 1H-imidazole; methanol; camphor-10-sulfonic acid; sodium; In N,N-dimethyl-formamide; acetone;
DOI:10.1016/j.tet.2004.06.009