(2S,3R,6R)-6-(benzyloxy)-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-ol

Base Information

• Chemical Name: (2S,3R,6R)-6-(benzyloxy)-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-ol
• CAS No.: 1385024-28-1
• Molecular Formula: C₁₃H₁₆O₄
• Molecular Weight: 236.268

Synonyms:(2S,3R,6R)-6-(benzyloxy)-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-ol

Chemical Property of (2S,3R,6R)-6-(benzyloxy)-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,6R)-6-(benzyloxy)-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-ol

There total 5 articles about (2S,3R,6R)-6-(benzyloxy)-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-ol 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:

2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-(2-furanyl)ethanone (691371-32-1) → (2S,3R,6R)-6-(benzyloxy)-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-ol (1385024-28-1)

Guidance literature:

Multi-step reaction with 6 steps

1: (1S,2S)-N-p-toluenesulfonyl-1,2-diphenylethylenediamine-ruthenium(mesitylene); sodium formate; cetyltrimethylammonim bromide / dichloromethane; water / 24 h / Inert atmosphere

2: N-Bromosuccinimide; sodium acetate; sodium hydrogencarbonate / tetrahydrofuran; water / 1 h / 0 °C

3: dmap / dichloromethane / 1 h / -78 °C

4: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; triphenylphosphine / dichloromethane / 1 h / 0 °C

5: sodium tetrahydroborate / methanol / 3 h / -78 °C

6: hydrogen fluoride / acetonitrile / 2 h / 0 °C

With dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium tetrahydroborate; N-Bromosuccinimide; (1S,2S)-N-p-toluenesulfonyl-1,2-diphenylethylenediamine-ruthenium(mesitylene); hydrogen fluoride; sodium formate; sodium acetate; cetyltrimethylammonim bromide; sodium hydrogencarbonate; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile;

DOI:10.1021/ja305321e

Reference yield:

(2S,6S)-carbonic acid tert-butyl ester 6-(tert-butyl-dimethyl-silanyloxymethyl)-4-oxo-2,3-dihydro-6H-pyran-2-yl ester (623157-43-7) → (2S,3R,6R)-6-(benzyloxy)-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-ol (1385024-28-1)

Guidance literature:

Multi-step reaction with 3 steps

1: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; triphenylphosphine / dichloromethane / 1 h / 0 °C

2: sodium tetrahydroborate / methanol / 3 h / -78 °C

3: hydrogen fluoride / acetonitrile / 2 h / 0 °C

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium tetrahydroborate; hydrogen fluoride; triphenylphosphine; In methanol; dichloromethane; acetonitrile;

DOI:10.1021/ja305321e

Reference yield:

(S)-2-((tert-butyldimethylsilyl)oxy)-1-(furan-2-yl)ethan-1-ol (222986-37-0) → (2S,3R,6R)-6-(benzyloxy)-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-ol (1385024-28-1)

Guidance literature:

Multi-step reaction with 5 steps

1: N-Bromosuccinimide; sodium acetate; sodium hydrogencarbonate / tetrahydrofuran; water / 1 h / 0 °C

2: dmap / dichloromethane / 1 h / -78 °C

3: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; triphenylphosphine / dichloromethane / 1 h / 0 °C

4: sodium tetrahydroborate / methanol / 3 h / -78 °C

5: hydrogen fluoride / acetonitrile / 2 h / 0 °C

With dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium tetrahydroborate; N-Bromosuccinimide; hydrogen fluoride; sodium acetate; sodium hydrogencarbonate; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile;

DOI:10.1021/ja305321e

upstream raw materials:

(S)-2-((tert-butyldimethylsilyl)oxy)-1-(furan-2-yl)ethan-1-ol

(2S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-6-hydroxy-2H-pyran-3(6H)-one

(2S,6R)-6-(benzyloxy)-2-(((tert-butyldimethylsilyl)oxy)methyl)-2H-pyran-3(6H)-one

(2S,6S)-carbonic acid tert-butyl ester 6-(tert-butyl-dimethyl-silanyloxymethyl)-4-oxo-2,3-dihydro-6H-pyran-2-yl ester

Downstream raw materials:

(2S,3R,6R)-6-(((2S,3R,6R)-6-(Benzyloxy)-2-((((2R,5R,6S)-6-(((tert-butyldimethylsilyl)oxy)methyl)-5-hydroxy-5,6-dihydro-2H-pyran-2-yl)oxy)methyl)-3,6-dihydro-2H-pyran-3-yl)oxy)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,6-dihydro-2H-pyran-3-ol

(2S,3R,6R)-6-(((2S,3R,6R)-6-(benzyloxy)-2-((((2R,5R,6S)-5-hydroxy-6-(hydroxymethyl)-5,6-dihydro-2H-pyran-2-yl)oxy)methyl)-3,6-dihydro-2H-pyran-3-yl)oxy)-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-ol

(2S,6R)-6-(((2S,3R,6R)-6-(benzyloxy)-2-((((2R,6S)-6-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxo-5,6-dihydro-2H-pyran-2-yl)oxy)methyl)-3,6-dihydro-2H-pyran-3-yl)oxy)-2-(((tert-butyldimethylsilyl)oxy)methyl)-2H-pyran-3(6H)-one

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