Methyl 4,6-O-Benzylidene-2-O-(tert-butyldimethylsilyl)-3-deoxy-3-C-((hydroxymethyl)methylene)-α-D-ribo-pyranoside

Base Information

Chemical Name:Methyl 4,6-O-Benzylidene-2-O-(tert-butyldimethylsilyl)-3-deoxy-3-C-((hydroxymethyl)methylene)-α-D-ribo-pyranoside
CAS No.:78329-11-0
Molecular Formula:C₂₂H₃₄O₆Si
Molecular Weight:422.594
Hs Code.:

Synonyms:Methyl 4,6-O-Benzylidene-2-O-(tert-butyldimethylsilyl)-3-deoxy-3-C-((hydroxymethyl)methylene)-α-D-ribo-pyranoside

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Chemical Property of Methyl 4,6-O-Benzylidene-2-O-(tert-butyldimethylsilyl)-3-deoxy-3-C-((hydroxymethyl)methylene)-α-D-ribo-pyranoside

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Technology Process of Methyl 4,6-O-Benzylidene-2-O-(tert-butyldimethylsilyl)-3-deoxy-3-C-((hydroxymethyl)methylene)-α-D-ribo-pyranoside

There total 5 articles about Methyl 4,6-O-Benzylidene-2-O-(tert-butyldimethylsilyl)-3-deoxy-3-C-((hydroxymethyl)methylene)-α-D-ribo-pyranoside 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: 90.0%

: 78342-22-0
Methyl 4,6-O-Benzylidene-2-O-(tert-butyldimethylsilyl)-3-deoxy-3-C-((E)-carbethoxymethylene)-α-D-ribo-hexopyranoside

: 78329-11-0
Methyl 4,6-O-Benzylidene-2-O-(tert-butyldimethylsilyl)-3-deoxy-3-C-((hydroxymethyl)methylene)-α-D-ribo-pyranoside

Guidance literature:: With diisobutylaluminium hydride; In toluene; at 0 ℃; for 0.5h;
DOI:10.1021/jo00187a010

Reference yield:

: 78329-10-9
Methyl 4,6-O-Benzylidene-2-O-(tert-butyldimethylsilyl)-α-D-ribo-hexopyranosid-3-uloside

: 78329-11-0
Methyl 4,6-O-Benzylidene-2-O-(tert-butyldimethylsilyl)-3-deoxy-3-C-((hydroxymethyl)methylene)-α-D-ribo-pyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 76 percent / acetonitrile / 24 h / Heating

2: 90 percent / diisobutylaluminum hydride / toluene / 0.5 h / 0 °C

With diisobutylaluminium hydride; In toluene; acetonitrile;
DOI:10.1021/jo00187a010

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 78329-11-0
Methyl 4,6-O-Benzylidene-2-O-(tert-butyldimethylsilyl)-3-deoxy-3-C-((hydroxymethyl)methylene)-α-D-ribo-pyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: Imidazole / dimethylformamide / 4 h / Ambient temperature

2: 80 percent / dimethylsulfoxide, trifluoracetic anhydride / CH₂Cl₂ / 0.5 h / -78 °C

3: 76 percent / acetonitrile / 24 h / Heating

4: 90 percent / diisobutylaluminum hydride / toluene / 0.5 h / 0 °C

With 1H-imidazole; diisobutylaluminium hydride; dimethyl sulfoxide; trifluoroacetic anhydride; In dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/jo00187a010