benzyl 2,3-O-[(2R,3R)-2,3-dimethoxybutane-2,3-dioxy]-β-L-arabinopyranoside

Base Information

• Chemical Name: benzyl 2,3-O-[(2R,3R)-2,3-dimethoxybutane-2,3-dioxy]-β-L-arabinopyranoside
• CAS No.: 550346-02-6
• Molecular Formula: C₁₈H₂₆O₇
• Molecular Weight: 354.4

Synonyms:benzyl 2,3-O-[(2R,3R)-2,3-dimethoxybutane-2,3-dioxy]-β-L-arabinopyranoside

Chemical Property of benzyl 2,3-O-[(2R,3R)-2,3-dimethoxybutane-2,3-dioxy]-β-L-arabinopyranoside

Chemical Property:

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Technology Process of benzyl 2,3-O-[(2R,3R)-2,3-dimethoxybutane-2,3-dioxy]-β-L-arabinopyranoside

There total 1 articles about benzyl 2,3-O-[(2R,3R)-2,3-dimethoxybutane-2,3-dioxy]-β-L-arabinopyranoside 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: 77.0%

2,2,3,3-tetramethoxybutane (176798-33-7) + benzyl β-L-arabinopyranoside (7473-38-3) → benzyl 2,3-O-[(2R,3R)-2,3-dimethoxybutane-2,3-dioxy]-β-L-arabinopyranoside (550346-02-6)

Guidance literature:

With camphor-10-sulfonic acid; trimethyl orthoformate; In methanol; for 8h; Heating;

DOI:10.1021/ol062873p

Reference yield: 100.0%

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate (990-91-0) + benzyl 2,3-O-[(2R,3R)-2,3-dimethoxybutane-2,3-dioxy]-β-L-arabinopyranoside (550346-02-6) → 1-O-benzyl-2,3-(2,3-dimethoxybut-2,3-diyl)-β-L-arabinopyranoside-4-O-dibenzylphosphate (1032939-14-2)

Guidance literature:

benzyl 2,3-O-[(2R,3R)-2,3-dimethoxybutane-2,3-dioxy]-β-L-arabinopyranoside; With potassium tert-butylate; In tetrahydrofuran; at 20 ℃; for 0.333333h; Inert atmosphere;

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate; In tetrahydrofuran; at -40 - 20 ℃; for 3.33333h;

DOI:10.1002/chem.200701351

Reference yield: 99.0%

pivaloyl chloride (3282-30-2) + benzyl 2,3-O-[(2R,3R)-2,3-dimethoxybutane-2,3-dioxy]-β-L-arabinopyranoside (550346-02-6) → 2,2-Dimethyl-propionic acid (2R,3R,4aR,5S,8S,8aS)-5-benzyloxy-2,3-dimethoxy-2,3-dimethyl-hexahydro-pyrano[3,4-b][1,4]dioxin-8-yl ester (550346-04-8)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1016/S0040-4020(03)00145-5

upstream raw materials:

2,2,3,3-tetramethoxybutane

benzyl β-L-arabinopyranoside

Downstream raw materials:

2,2-Dimethyl-propionic acid (2R,3R,4aR,5S,8S,8aS)-5-benzyloxy-2,3-dimethoxy-2,3-dimethyl-hexahydro-pyrano[3,4-b][1,4]dioxin-8-yl ester

Benzoic acid (2R,3R,4aR,5S,8S,8aS)-5-benzyloxy-2,3-dimethoxy-2,3-dimethyl-hexahydro-pyrano[3,4-b][1,4]dioxin-8-yl ester

(2R,3R,4aR,5S,8S,8aS)-5-Benzyloxy-2,3-diisobutoxy-2,3-dimethyl-hexahydro-pyrano[3,4-b][1,4]dioxin-8-ol

(2R,3R,4aR,5S,8S,8aS)-5-Benzyloxy-2,3-dimethyl-2,3-bis-(3-methyl-butoxy)-hexahydro-pyrano[3,4-b][1,4]dioxin-8-ol

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