3,5-di-O-benzyl-4-C-(hydroxymethyl)-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribofuranose

Base Information

Chemical Name:3,5-di-O-benzyl-4-C-(hydroxymethyl)-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribofuranose
CAS No.:879546-88-0
Molecular Formula:C₂₅H₃₀O₆
Molecular Weight:426.51
Hs Code.:

Synonyms:3,5-di-O-benzyl-4-C-(hydroxymethyl)-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribofuranose

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Chemical Property of 3,5-di-O-benzyl-4-C-(hydroxymethyl)-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribofuranose

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Technology Process of 3,5-di-O-benzyl-4-C-(hydroxymethyl)-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribofuranose

There total 5 articles about 3,5-di-O-benzyl-4-C-(hydroxymethyl)-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribofuranose 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%

: 879546-87-9
3-O-benzyl-4-C-(hydroxymethyl)-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribofuranose

: 100-39-0
benzyl bromide

: 879546-88-0
3,5-di-O-benzyl-4-C-(hydroxymethyl)-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribofuranose

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide;
DOI:10.1080/15257770701542975

Reference yield: 60.0%

: 879546-87-9
3-O-benzyl-4-C-(hydroxymethyl)-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribofuranose

: 100-39-0
benzyl bromide

: 879546-88-0
3,5-di-O-benzyl-4-C-(hydroxymethyl)-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribofuranose

: 1107055-80-0
3-O-benzyl-4-C-(benzyloxymethyl)-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribofuranose

Guidance literature:: 3-O-benzyl-4-C-(hydroxymethyl)-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribofuranose; With sodium hydride; In N,N-dimethyl-formamide; oil; at -20 ℃; for 0.5h; Inert atmosphere;

benzyl bromide; In N,N-dimethyl-formamide; oil; at -20 ℃; for 0.5h; Inert atmosphere;
DOI:10.1002/ejoc.200800716

Reference yield:

: (3aR,5S,6R,6aR)-6-(benzyloxy)-2,2-dimethyl-6-vinyltetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde

: 879546-88-0
3,5-di-O-benzyl-4-C-(hydroxymethyl)-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribofuranose

Guidance literature:: Multi-step reaction with 2 steps

1: 562 mg / sodium hydroxide / tetrahydrofuran; H₂O / 18 h / 20 °C

2: 54 percent / sodium hydride / dimethylformamide / 1.5 h / 20 °C

With sodium hydroxide; sodium hydride; In tetrahydrofuran; water; N,N-dimethyl-formamide; 1: aldol-Cannizzaro reaction;
DOI:10.1021/jo051187l