benzyl-6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-glycero-hex-2-enopyranosid-4-ulose

Base Information

• Chemical Name: benzyl-6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-glycero-hex-2-enopyranosid-4-ulose
• CAS No.: 81389-89-1
• Molecular Formula: C₁₉H₂₈O₄Si
• Molecular Weight: 348.514
• Mol file: 81389-89-1.mol

Synonyms:benzyl-6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-glycero-hex-2-enopyranosid-4-ulose

Chemical Property of benzyl-6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-glycero-hex-2-enopyranosid-4-ulose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl-6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-glycero-hex-2-enopyranosid-4-ulose

There total 8 articles about benzyl-6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-glycero-hex-2-enopyranosid-4-ulose 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: 92.0%

(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) + benzyl alcohol (100-51-6,185532-71-2) → benzyl-6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-glycero-hex-2-enopyranosid-4-ulose (81389-89-1)

Guidance literature:

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; triphenylphosphine; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1021/ja305321e

Reference yield: 80.0%

(2R,6R)-6-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxo-5,6-dihydro-2H-pyran-2-yl 2-phenylacetate + benzyl alcohol (100-51-6,185532-71-2) → benzyl-6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-glycero-hex-2-enopyranosid-4-ulose (81389-89-1)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; triphenylphosphine; In dichloromethane; at 0 ℃; for 2h; stereospecific reaction; Inert atmosphere;

DOI:10.1021/acs.orglett.5b02641

Reference yield: 76.0%

(2R,3S,6S)-6-(benzyloxy)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,6-dihydro-2H-pyran-3-ol (81389-87-9) → benzyl-6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-glycero-hex-2-enopyranosid-4-ulose (81389-89-1)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; for 24h; Ambient temperature;

DOI:10.1021/jo00132a037

upstream raw materials:

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

benzyl 4,6-di-O-acetyl-2,3-dideoxy-α/β-D-erythro-hex-2-enopyranoside

(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

Downstream raw materials:

<1S-(1α,3β)>-3-<(tert-butyldimethylsiloxy)methyl>-3,4-dihydro-1-(benzyloxy)-5-hydroxy-1H-2-benzopyran-4-one

(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

(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