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

Base Information

• Chemical Name: (2S,6R)-6-(((2R,3S,6S)-6-(benzyloxy)-2-((((2R,6S)-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl)oxy)methyl)-3,6-dihydro-2H-pyran-3-yl)oxy)-2-methyl-2H-pyran-3(6H)-one
• CAS No.: 1385024-24-7
• Molecular Formula: C₂₅H₂₈O₈
• Molecular Weight: 456.493
• Mol file: 1385024-24-7.mol

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

Chemical Property of (2S,6R)-6-(((2R,3S,6S)-6-(benzyloxy)-2-((((2R,6S)-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl)oxy)methyl)-3,6-dihydro-2H-pyran-3-yl)oxy)-2-methyl-2H-pyran-3(6H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of (2S,6R)-6-(((2R,3S,6S)-6-(benzyloxy)-2-((((2R,6S)-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl)oxy)methyl)-3,6-dihydro-2H-pyran-3-yl)oxy)-2-methyl-2H-pyran-3(6H)-one

There total 7 articles about (2S,6R)-6-(((2R,3S,6S)-6-(benzyloxy)-2-((((2R,6S)-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl)oxy)methyl)-3,6-dihydro-2H-pyran-3-yl)oxy)-2-methyl-2H-pyran-3(6H)-one 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: 75.0%

tert-butyl ((2S,6S)-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl) carbonate (865484-73-7) + (2R,3S,6S)-6-(benzyloxy)-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-ol (81389-86-8) → (2S,6R)-6-(((2R,3S,6S)-6-(benzyloxy)-2-((((2R,6S)-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl)oxy)methyl)-3,6-dihydro-2H-pyran-3-yl)oxy)-2-methyl-2H-pyran-3(6H)-one (1385024-24-7)

Guidance literature:

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; triphenylphosphine; In dichloromethane; at 0 ℃; for 3h; diastereoselective reaction;

DOI:10.1021/ja305321e

Reference yield:

(2R,6R)-carbonic acid tert-butyl ester 6-(tert-butyl-dimethyl-silanyloxymethyl)-4-oxo-2,3-dihydro-6H-pyran-2-yl ester (862255-90-1) → (2S,6R)-6-(((2R,3S,6S)-6-(benzyloxy)-2-((((2R,6S)-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl)oxy)methyl)-3,6-dihydro-2H-pyran-3-yl)oxy)-2-methyl-2H-pyran-3(6H)-one (1385024-24-7)

Guidance literature:

Multi-step reaction with 4 steps

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

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

3: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 °C

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

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium tetrahydroborate; tetrabutyl ammonium fluoride; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/ja305321e

Reference yield:

(2R,3S,6S)-6-(benzyloxy)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,6-dihydro-2H-pyran-3-ol (81389-87-9) → (2S,6R)-6-(((2R,3S,6S)-6-(benzyloxy)-2-((((2R,6S)-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl)oxy)methyl)-3,6-dihydro-2H-pyran-3-yl)oxy)-2-methyl-2H-pyran-3(6H)-one (1385024-24-7)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 °C

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

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; tetrabutyl ammonium fluoride; triphenylphosphine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja305321e

upstream raw materials:

tert-butyl ((2S,6S)-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl) carbonate

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

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

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

Downstream raw materials:

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

(2S,3R,4R,5R,6S)-2-(((2R,3S,4R,5S,6S)-6-(benzyloxy)-4,5-dihydroxy-2-((((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-3-yl)oxy)-6-methyltetrahydro-2H-pyran-3,4,5-triol

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