(1S,2R,3S,5R)-2-benzyloxymethyl-3-(4-methoxybenzyloxy)-6-oxabicyclo<3.1.0>hexane

Base Information

• Chemical Name: (1S,2R,3S,5R)-2-benzyloxymethyl-3-(4-methoxybenzyloxy)-6-oxabicyclo<3.1.0>hexane
• CAS No.: 133299-26-0
• Molecular Formula: C₂₁H₂₄O₄
• Molecular Weight: 340.419
• Mol file: 133299-26-0.mol

Synonyms:(1S,2R,3S,5R)-2-benzyloxymethyl-3-(4-methoxybenzyloxy)-6-oxabicyclo<3.1.0>hexane

Chemical Property of (1S,2R,3S,5R)-2-benzyloxymethyl-3-(4-methoxybenzyloxy)-6-oxabicyclo<3.1.0>hexane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1S,2R,3S,5R)-2-benzyloxymethyl-3-(4-methoxybenzyloxy)-6-oxabicyclo<3.1.0>hexane

There total 2 articles about (1S,2R,3S,5R)-2-benzyloxymethyl-3-(4-methoxybenzyloxy)-6-oxabicyclo<3.1.0>hexane 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: 95.0%

p-Methoxybenzyl bromide (2746-25-0) + (2R,3S)-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexan-3-ol (117641-39-1) → (1S,2R,3S,5R)-2-benzyloxymethyl-3-(4-methoxybenzyloxy)-6-oxabicyclo<3.1.0>hexane (133299-26-0)

Guidance literature:

(2R,3S)-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexan-3-ol; With sodium hydride; In tetrahydrofuran; at 0 - 20 ℃; for 0.5h;

p-Methoxybenzyl bromide; With tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; for 24h;

DOI:10.1016/j.bmc.2014.07.051

Reference yield: 85.0%

(2R,3S)-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexan-3-ol (117641-39-1) + p-methoxybenzyl chloride (824-94-2) → (1S,2R,3S,5R)-2-benzyloxymethyl-3-(4-methoxybenzyloxy)-6-oxabicyclo<3.1.0>hexane (133299-26-0)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2003.11.052

Reference yield: 84.0%

(1S,2R,3S,5R)-2-benzyloxymethyl-3-(4-methoxybenzyloxy)-6-oxabicyclo<3.1.0>hexane (133299-26-0) → (1R,4S,5S)-5-((benzyloxy)methyl)-4-((4-methoxybenzyl)oxy)cyclopent-2-enol (668996-17-6)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at 60 ℃; for 3h; regioselective reaction;

DOI:10.1016/j.bmc.2014.07.051

upstream raw materials:

(2R,3S)-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexan-3-ol

p-methoxybenzyl chloride

p-Methoxybenzyl bromide

Downstream raw materials:

(1S,2R,3S,5S)-5-<2-amino-6-(2-methoxyethoxy)-9H-purin-9-yl>-2-benzyloxymethyl-3-(4-methoxybenzyloxy)cyclopentanol

(1R,4S,5S)-5-((benzyloxy)methyl)-4-((4-methoxybenzyl)oxy)cyclopent-2-enol

(R)-4-hydroxy-2-benzyloxymethylcyclopent-2-en-1-one

<1(R)-(1α,4α,5β)>-5-<(benzyloxy)methyl>-4-<(tert-butyldimethylsilyl)oxy>-2-cyclopenten-1-ol