3-O-benzyl-5-(O-tert-butyldiphenylsilyl)-4-C-(Z)-prop-1-enyl-1,2-O-isopropylidene-α-D-ribofuranose

Base Information

Chemical Name:3-O-benzyl-5-(O-tert-butyldiphenylsilyl)-4-C-(Z)-prop-1-enyl-1,2-O-isopropylidene-α-D-ribofuranose
CAS No.:1421238-34-7
Molecular Formula:C₃₄H₄₂O₅Si
Molecular Weight:558.79
Hs Code.:

Synonyms:3-O-benzyl-5-(O-tert-butyldiphenylsilyl)-4-C-(Z)-prop-1-enyl-1,2-O-isopropylidene-α-D-ribofuranose

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Chemical Property of 3-O-benzyl-5-(O-tert-butyldiphenylsilyl)-4-C-(Z)-prop-1-enyl-1,2-O-isopropylidene-α-D-ribofuranose

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Technology Process of 3-O-benzyl-5-(O-tert-butyldiphenylsilyl)-4-C-(Z)-prop-1-enyl-1,2-O-isopropylidene-α-D-ribofuranose

There total 1 articles about 3-O-benzyl-5-(O-tert-butyldiphenylsilyl)-4-C-(Z)-prop-1-enyl-1,2-O-isopropylidene-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: 84.0%

: 1530-32-1
ethyltriphenylphosphonium bromide

: 454715-80-1
5-O-(tert-butyldiphenylsilyl)-3-O-benzyl-4-C-formyl-1,2-O-isopropylidene-α-D-erythropentofuranose

: 1421238-34-7
3-O-benzyl-5-(O-tert-butyldiphenylsilyl)-4-C-(Z)-prop-1-enyl-1,2-O-isopropylidene-α-D-ribofuranose

Guidance literature:: ethyltriphenylphosphonium bromide; With potassium tert-butylate; In tetrahydrofuran; at 20 ℃; for 2h;

5-O-(tert-butyldiphenylsilyl)-3-O-benzyl-4-C-formyl-1,2-O-isopropylidene-α-D-erythropentofuranose; In tetrahydrofuran; for 17h;
DOI:10.3998/ark.5550190.0014.206

Reference yield: 64.0%

: 1421238-34-7
3-O-benzyl-5-(O-tert-butyldiphenylsilyl)-4-C-(Z)-prop-1-enyl-1,2-O-isopropylidene-α-D-ribofuranose

: 108-24-7
acetic anhydride

: 1421238-35-8
1,2-di-O-acetyl-3-O-benzyl-5-(O-tert-butyldiphenylsilyl)-4-C-(Z)-prop-1-enyl-α,β-D-ribofuranose

Guidance literature:: With sulfuric acid; In acetic acid; at 20 ℃; for 24h;
DOI:10.3998/ark.5550190.0014.206

Reference yield:

: 1421238-34-7
3-O-benzyl-5-(O-tert-butyldiphenylsilyl)-4-C-(Z)-prop-1-enyl-1,2-O-isopropylidene-α-D-ribofuranose

: C₃₅H₄₂N₂O₅Si

Guidance literature:: Multi-step reaction with 4 steps

1.1: sulfuric acid / acetic acid / 24 h / 20 °C

2.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 1 h / 20 °C / Reflux

2.2: 1 h / Reflux

3.1: sodium methylate / methanol / 2 h / 20 °C

4.1: 10% Pd/C; hydrogen / ethanol / 8 h / 20 °C

With N,O-bis-(trimethylsilyl)-acetamide; sulfuric acid; 10% Pd/C; hydrogen; sodium methylate; In methanol; ethanol; acetic acid; acetonitrile;
DOI:10.3998/ark.5550190.0014.206