6-deoxy-2-O-(p-methoxybenzyl)-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-5a-carba-α-D-lyxo-hex-5-enopyranoside

Base Information

Chemical Name:6-deoxy-2-O-(p-methoxybenzyl)-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-5a-carba-α-D-lyxo-hex-5-enopyranoside
CAS No.:1392067-23-0
Molecular Formula:C₂₁H₃₀O₇
Molecular Weight:394.465
Hs Code.:

Synonyms:6-deoxy-2-O-(p-methoxybenzyl)-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-5a-carba-α-D-lyxo-hex-5-enopyranoside

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Chemical Property of 6-deoxy-2-O-(p-methoxybenzyl)-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-5a-carba-α-D-lyxo-hex-5-enopyranoside

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Technology Process of 6-deoxy-2-O-(p-methoxybenzyl)-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-5a-carba-α-D-lyxo-hex-5-enopyranoside

There total 7 articles about 6-deoxy-2-O-(p-methoxybenzyl)-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-5a-carba-α-D-lyxo-hex-5-enopyranoside 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: 86.0%

: Tebbe's reagent

: 1392067-14-9
(2S,3S,4aS,7S,8R,8aR)-7-hydroxy-2,3-dimethoxy-8-((pmethoxybenzyl)oxy)-2,3-dimethylhexahydrobenzo[b][1,4]dioxin-5-(4aH)-one

: 1392067-23-0
6-deoxy-2-O-(p-methoxybenzyl)-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-5a-carba-α-D-lyxo-hex-5-enopyranoside

Guidance literature:: In tetrahydrofuran; toluene; at 0 - 20 ℃; for 2h; Inert atmosphere;
DOI:10.1021/jo301240j

Reference yield: 85.0%

: 1392067-14-9
(2S,3S,4aS,7S,8R,8aR)-7-hydroxy-2,3-dimethoxy-8-((pmethoxybenzyl)oxy)-2,3-dimethylhexahydrobenzo[b][1,4]dioxin-5-(4aH)-one

: 1779-49-3
Methyltriphenylphosphonium bromide

: 1392067-23-0
6-deoxy-2-O-(p-methoxybenzyl)-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-5a-carba-α-D-lyxo-hex-5-enopyranoside

Guidance literature:: Methyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; hexane; at 0 - 20 ℃; for 1h; Inert atmosphere;

(2S,3S,4aS,7S,8R,8aR)-7-hydroxy-2,3-dimethoxy-8-((pmethoxybenzyl)oxy)-2,3-dimethylhexahydrobenzo[b][1,4]dioxin-5-(4aH)-one; In tetrahydrofuran; hexane; at 0 - 20 ℃; for 2h; Inert atmosphere;
DOI:10.1021/jo301240j

Reference yield:

: 197577-12-1
methyl 6-deoxy-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-6-iodo-α-D-mannoside

: 1392067-23-0
6-deoxy-2-O-(p-methoxybenzyl)-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-5a-carba-α-D-lyxo-hex-5-enopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: (1S)-(+)-camphorsulfonic acid monohydrate / dichloromethane / 16 h / 20 °C

2.1: potassium tert-butylate / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

3.1: palladium dichloride / 1,4-dioxane; water / 3 h / 60 °C / Inert atmosphere

4.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 - 20 °C / Inert atmosphere

4.2: 2 h / 0 - 20 °C / Inert atmosphere

With n-butyllithium; (1S)-(+)-camphorsulfonic acid monohydrate; potassium tert-butylate; palladium dichloride; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; water; 4.1: |Wittig Olefination;
DOI:10.1021/jo301240j