benzyl 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: benzyl 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.: 1392067-25-2
• Molecular Formula: C₂₈H₃₆O₇
• Molecular Weight: 484.59

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 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 benzyl 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: 90.0%

6-deoxy-2-O-(p-methoxybenzyl)-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-5a-carba-α-D-lyxo-hex-5-enopyranoside (1392067-23-0) + benzyl bromide (100-39-0) → benzyl 6-deoxy-2-O-(p-methoxybenzyl)-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-5a-carba-α-D-lyxo-hex-5-enopyranoside (1392067-25-2)

Guidance literature:

6-deoxy-2-O-(p-methoxybenzyl)-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-5a-carba-α-D-lyxo-hex-5-enopyranoside; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.166667h; Inert atmosphere;

benzyl bromide; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 3h; Inert atmosphere;

DOI:10.1021/jo301240j

Reference yield:

methyl 6-deoxy-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-6-iodo-α-D-mannoside (197577-12-1) → benzyl 6-deoxy-2-O-(p-methoxybenzyl)-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-5a-carba-α-D-lyxo-hex-5-enopyranoside (1392067-25-2)

Guidance literature:

Multi-step reaction with 5 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: tetrahydrofuran; toluene / 2 h / 0 - 20 °C / Inert atmosphere

5.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 0 °C / Inert atmosphere

5.2: 3 h / 0 - 20 °C / Inert atmosphere

With (1S)-(+)-camphorsulfonic acid monohydrate; potassium tert-butylate; sodium hydride; palladium dichloride; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo301240j

Reference yield:

(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 (1252047-54-3) → benzyl 6-deoxy-2-O-(p-methoxybenzyl)-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-5a-carba-α-D-lyxo-hex-5-enopyranoside (1392067-25-2)

Guidance literature:

Multi-step reaction with 4 steps

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

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

3.1: tetrahydrofuran; toluene / 2 h / 0 - 20 °C / Inert atmosphere

4.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 0 °C / Inert atmosphere

4.2: 3 h / 0 - 20 °C / Inert atmosphere

With potassium tert-butylate; sodium hydride; palladium dichloride; In tetrahydrofuran; 1,4-dioxane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo301240j

upstream raw materials:

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

(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

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

benzyl bromide

Downstream raw materials:

(2S,3S,4aR,5S,7S,8R,8aR)-7-(benzyloxy)-8-hydroxy-2,3-dimethoxy-2,3-dimethyloctahydrobenzo[b][1,4]dioxine-5-carbaldehyde

(2S,3S,4aR,5R,7S,8R,8aS)-7-(benzyloxy)-2,3-dimethoxy-8-((4-methoxybenzyl)oxy)-2,3-dimethyloctahydrobenzo[b][1,4]dioxine-5-carbaldehyde

(2S,3S,4aR,5S,7S,8R,8aS)-7-(benzyloxy)-2,3-dimethoxy-8-((4-methoxybenzyl)oxy)-2,3-dimethyloctahydrobenzo[b][1,4]dioxine-5-carbaldehyde

1-O-benzyl-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-5a-carba-α-D-manuronic acid

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