[1R-(1α,2α,3β,4α,5α)]-2,3,4-tris(benzyloxy)-1-(hydroxymethyl)-6-oxabicyclo[3.1.0]hexane

Base Information

Chemical Name:[1R-(1α,2α,3β,4α,5α)]-2,3,4-tris(benzyloxy)-1-(hydroxymethyl)-6-oxabicyclo[3.1.0]hexane
CAS No.:213338-06-8
Molecular Formula:C₂₇H₂₈O₅
Molecular Weight:432.516
Hs Code.:

Synonyms:[1R-(1α,2α,3β,4α,5α)]-2,3,4-tris(benzyloxy)-1-(hydroxymethyl)-6-oxabicyclo[3.1.0]hexane

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Chemical Property of [1R-(1α,2α,3β,4α,5α)]-2,3,4-tris(benzyloxy)-1-(hydroxymethyl)-6-oxabicyclo[3.1.0]hexane

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Technology Process of [1R-(1α,2α,3β,4α,5α)]-2,3,4-tris(benzyloxy)-1-(hydroxymethyl)-6-oxabicyclo[3.1.0]hexane

There total 11 articles about [1R-(1α,2α,3β,4α,5α)]-2,3,4-tris(benzyloxy)-1-(hydroxymethyl)-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: 93.0%

: 213338-04-6
[3S-(3α,4β,5α)]-3,4,5-tris(benzyloxy)-1-(hydroxymethyl)-1-cyclopentene

: 213338-06-8
[1R-(1α,2α,3β,4α,5α)]-2,3,4-tris(benzyloxy)-1-(hydroxymethyl)-6-oxabicyclo[3.1.0]hexane

Guidance literature:: With titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate; In decane; dichloromethane; at -30 ℃; for 20h;
DOI:10.1021/jo980831b

Reference yield:

: 4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9
2,3,4,6-Tetra-O-benzyl-D-glucopyranose

: 213338-06-8
[1R-(1α,2α,3β,4α,5α)]-2,3,4-tris(benzyloxy)-1-(hydroxymethyl)-6-oxabicyclo[3.1.0]hexane

Guidance literature:: Multi-step reaction with 8 steps

1: 98 percent / NaBH₄ / ethanol; CH₂Cl₂ / 20 °C

2: (COCl)2; DMSO; Et₃N / tetrahydrofuran / 1.75 h / -65 - 20 °C

3: 3.54 g / SmI₂; t-BuOH / tetrahydrofuran / -50 - 20 °C

4: 45 percent / toluene / 4 h / 110 °C

5: 88 percent / TMSOTf / 17 h / 20 °C

6: 97 percent / (EtO)3P / 3 h / 155 °C

7: 96 percent / NaOMe / CH₂Cl₂; methanol / 1 h / 20 °C

8: 93 percent / diisopropyl L-tartrate; titanium tetraisopropoxide; tert-butyl hydroperoxide / CH₂Cl₂; decane / 20 h / -30 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium tetrahydroborate; samarium diiodide; oxalyl dichloride; L-(+)-diisopropyl tartrate; trimethylsilyl trifluoromethanesulfonate; sodium methylate; dimethyl sulfoxide; triethylamine; tert-butyl alcohol; triethyl phosphite; In tetrahydrofuran; methanol; decane; ethanol; dichloromethane; toluene; 1: Reduction / 2: Swern oxidation / 3: Cyclization / 4: Cyclization / 5: acetolysis / 6: Elimination / 7: Deacetylation / 8: Sharpless epoxidation;
DOI:10.1021/jo980831b

Reference yield:

: 78136-16-0,14233-48-8
2,3,4,6-tetra-O-benzyl-D-glucitol

: 213338-06-8
[1R-(1α,2α,3β,4α,5α)]-2,3,4-tris(benzyloxy)-1-(hydroxymethyl)-6-oxabicyclo[3.1.0]hexane

Guidance literature:: Multi-step reaction with 7 steps

1: (COCl)2; DMSO; Et₃N / tetrahydrofuran / 1.75 h / -65 - 20 °C

2: 3.54 g / SmI₂; t-BuOH / tetrahydrofuran / -50 - 20 °C

3: 45 percent / toluene / 4 h / 110 °C

4: 88 percent / TMSOTf / 17 h / 20 °C

5: 97 percent / (EtO)3P / 3 h / 155 °C

6: 96 percent / NaOMe / CH₂Cl₂; methanol / 1 h / 20 °C

7: 93 percent / diisopropyl L-tartrate; titanium tetraisopropoxide; tert-butyl hydroperoxide / CH₂Cl₂; decane / 20 h / -30 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; samarium diiodide; oxalyl dichloride; L-(+)-diisopropyl tartrate; trimethylsilyl trifluoromethanesulfonate; sodium methylate; dimethyl sulfoxide; triethylamine; tert-butyl alcohol; triethyl phosphite; In tetrahydrofuran; methanol; decane; dichloromethane; toluene; 1: Swern oxidation / 2: Cyclization / 3: Cyclization / 4: acetolysis / 5: Elimination / 6: Deacetylation / 7: Sharpless epoxidation;
DOI:10.1021/jo980831b