(2'S,3'S)-methyl 6-deoxy-2-O-(4-methoxybenzyl)-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-iodo-α-D-mannopyranoside

Base Information

Chemical Name:(2'S,3'S)-methyl 6-deoxy-2-O-(4-methoxybenzyl)-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-iodo-α-D-mannopyranoside
CAS No.:1252047-54-3
Molecular Formula:C₂₁H₃₁IO₈
Molecular Weight:538.377
Hs Code.:

Synonyms:(2'S,3'S)-methyl 6-deoxy-2-O-(4-methoxybenzyl)-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-iodo-α-D-mannopyranoside

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Chemical Property of (2'S,3'S)-methyl 6-deoxy-2-O-(4-methoxybenzyl)-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-iodo-α-D-mannopyranoside

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Technology Process of (2'S,3'S)-methyl 6-deoxy-2-O-(4-methoxybenzyl)-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-iodo-α-D-mannopyranoside

There total 3 articles about (2'S,3'S)-methyl 6-deoxy-2-O-(4-methoxybenzyl)-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-iodo-α-D-mannopyranoside 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: 93.0%

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

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

: 1252047-54-3
(2'S,3'S)-methyl 6-deoxy-2-O-(4-methoxybenzyl)-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-iodo-α-D-mannopyranoside

Guidance literature:: With (1S)-(+)-camphorsulfonic acid monohydrate; In dichloromethane; at 20 ℃; for 16h;
DOI:10.1021/jo301240j

Reference yield: 78.0%

: 1252047-52-1
(2'S,3'S)-methyl 2-O-(4-methoxybenzyl)-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-α-D-mannopyranoside

: 1252047-54-3
(2'S,3'S)-methyl 6-deoxy-2-O-(4-methoxybenzyl)-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-iodo-α-D-mannopyranoside

Guidance literature:: With 1H-imidazole; iodine; triphenylphosphine; In toluene; at 70 ℃; for 4h; Inert atmosphere;
DOI:10.1016/j.tet.2010.07.037

Reference yield:

: 617-04-9
(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol

: 1252047-54-3
(2'S,3'S)-methyl 6-deoxy-2-O-(4-methoxybenzyl)-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-iodo-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: (1S)-10-camphorsulfonic acid / methanol / 17 h / Reflux

2: triphenylphosphine; 1H-imidazole; iodine / tetrahydrofuran / Reflux

3: (1S)-(+)-camphorsulfonic acid monohydrate / dichloromethane / 16 h / 20 °C

With 1H-imidazole; (1S)-(+)-camphorsulfonic acid monohydrate; (1S)-10-camphorsulfonic acid; iodine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo301240j