3-O-benzyl-6-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-α-D-xylo-hexofuran-5-ulose

Base Information

Chemical Name:3-O-benzyl-6-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-α-D-xylo-hexofuran-5-ulose
CAS No.:106445-05-0
Molecular Formula:C₂₂H₃₄O₆Si
Molecular Weight:422.594
Hs Code.:

Synonyms:3-O-benzyl-6-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-α-D-xylo-hexofuran-5-ulose

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Chemical Property of 3-O-benzyl-6-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-α-D-xylo-hexofuran-5-ulose

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Technology Process of 3-O-benzyl-6-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-α-D-xylo-hexofuran-5-ulose

There total 5 articles about 3-O-benzyl-6-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-α-D-xylo-hexofuran-5-ulose 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:

: 106445-04-9
1-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyldimethylsiloxy)ethanol

: 106445-05-0
3-O-benzyl-6-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-α-D-xylo-hexofuran-5-ulose

Guidance literature:: With dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; Yield given. Multistep reaction; 1) CH₂CL₂, -78 deg C, 15 min, 2) CH₂Cl₂, -78 deg C, 45 min, 3) CH₂Cl₂, -78 deg C, 1 h then RT;
DOI:10.1139/v86-296

Reference yield:

: 22529-61-9
(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

: 106445-05-0
3-O-benzyl-6-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-α-D-xylo-hexofuran-5-ulose

Guidance literature:: Multi-step reaction with 2 steps

1: Et₃N, DMAP / CH₂Cl₂ / 18 h / Ambient temperature

2: (COCl)2, DMSO

With dmap; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane;
DOI:10.1039/a800486b

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 106445-05-0
3-O-benzyl-6-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-α-D-xylo-hexofuran-5-ulose

Guidance literature:: Multi-step reaction with 2 steps

1: imidazole / dimethylformamide / 4 h / Ambient temperature

2: 1.) oxalyl chloride, DMSO, 2.) Et₃N / -78 deg C, 2 h

With 1H-imidazole; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In N,N-dimethyl-formamide;
DOI:10.1016/0040-4039(93)85033-S