(1S,3R,4R,5S,6R)-4,5-bis((4-methoxybenzyl)oxy)-3-(((4-methoxybenzyl)oxy)methyl)-2,7-dioxabicyclo[4.1.0]heptane

Base Information

• Chemical Name: (1S,3R,4R,5S,6R)-4,5-bis((4-methoxybenzyl)oxy)-3-(((4-methoxybenzyl)oxy)methyl)-2,7-dioxabicyclo[4.1.0]heptane
• CAS No.: 316790-20-2
• Molecular Formula: C₃₀H₃₄O₈
• Molecular Weight: 522.595

Synonyms:(1S,3R,4R,5S,6R)-4,5-bis((4-methoxybenzyl)oxy)-3-(((4-methoxybenzyl)oxy)methyl)-2,7-dioxabicyclo[4.1.0]heptane

Chemical Property of (1S,3R,4R,5S,6R)-4,5-bis((4-methoxybenzyl)oxy)-3-(((4-methoxybenzyl)oxy)methyl)-2,7-dioxabicyclo[4.1.0]heptane

Chemical Property:

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Technology Process of (1S,3R,4R,5S,6R)-4,5-bis((4-methoxybenzyl)oxy)-3-(((4-methoxybenzyl)oxy)methyl)-2,7-dioxabicyclo[4.1.0]heptane

There total 3 articles about (1S,3R,4R,5S,6R)-4,5-bis((4-methoxybenzyl)oxy)-3-(((4-methoxybenzyl)oxy)methyl)-2,7-dioxabicyclo[4.1.0]heptane 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:

1,5-anhydro-2-deoxy-3,4,6-tri-O-(4-methoxybenzyl)-D-arabino-hex-1-enitol (219932-11-3) → (1S,3R,4R,5S,6R)-4,5-bis((4-methoxybenzyl)oxy)-3-(((4-methoxybenzyl)oxy)methyl)-2,7-dioxabicyclo[4.1.0]heptane (316790-20-2)

Guidance literature:

With 3,3-dimethyldioxirane; In dichloromethane; acetone; at -25 ℃;

DOI:10.1021/jo0012952

Reference yield:

p-methoxybenzyl chloride (824-94-2) → (1S,3R,4R,5S,6R)-4,5-bis((4-methoxybenzyl)oxy)-3-(((4-methoxybenzyl)oxy)methyl)-2,7-dioxabicyclo[4.1.0]heptane (316790-20-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaH / dimethylformamide / 0.5 h / 0 °C

1.2: 76 percent / (n-Bu)4NI / dimethylformamide / 0 h / 20 °C

2.1: dimethyldioxirane / CH₂Cl₂; acetone / -25 °C

With 3,3-dimethyldioxirane; sodium hydride; In dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jo0012952

Reference yield:

D-glucal (13265-84-4) → (1S,3R,4R,5S,6R)-4,5-bis((4-methoxybenzyl)oxy)-3-(((4-methoxybenzyl)oxy)methyl)-2,7-dioxabicyclo[4.1.0]heptane (316790-20-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaH / dimethylformamide / 0.5 h / 0 °C

1.2: 76 percent / (n-Bu)4NI / dimethylformamide / 0 h / 20 °C

2.1: dimethyldioxirane / CH₂Cl₂; acetone / -25 °C

With 3,3-dimethyldioxirane; sodium hydride; In dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jo0012952

upstream raw materials:

1,5-anhydro-2-deoxy-3,4,6-tri-O-(4-methoxybenzyl)-D-arabino-hex-1-enitol

p-methoxybenzyl chloride

D-glucal

Downstream raw materials:

(2R,3R,4R,5R,6R)-2-azido-4,5-bis(4-methoxybenzyloxy)-6-((4-methoxybenzyloxy)methyl)tetrahydro-2H-pyran-3-ol

daidzein-7-O-α-D-glucopyranosyl-(1-> 4)-O-β-D-glucopyranoside

undec-9-ynoic acid 6-[4,5-bis-(4-methoxy-benzyloxy)-6-(4-methoxy-benzyloxymethyl)-2-(1-methyl-dec-8-ynyloxy)-tetrahydro-pyran-3-yloxy]-4,5-bis-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yl ester

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