Methyl 4,6-O-Benzylidene-3-O-(tert-butyldimethylsilyl)-2-deoxy-2-C-(formylmethyl)-2-C-vinyl-α-D-glucopyranoside

Base Information

Chemical Name:Methyl 4,6-O-Benzylidene-3-O-(tert-butyldimethylsilyl)-2-deoxy-2-C-(formylmethyl)-2-C-vinyl-α-D-glucopyranoside
CAS No.:78329-24-5
Molecular Formula:C₂₄H₃₆O₆Si
Molecular Weight:448.632
Hs Code.:

Synonyms:Methyl 4,6-O-Benzylidene-3-O-(tert-butyldimethylsilyl)-2-deoxy-2-C-(formylmethyl)-2-C-vinyl-α-D-glucopyranoside

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Chemical Property of Methyl 4,6-O-Benzylidene-3-O-(tert-butyldimethylsilyl)-2-deoxy-2-C-(formylmethyl)-2-C-vinyl-α-D-glucopyranoside

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Technology Process of Methyl 4,6-O-Benzylidene-3-O-(tert-butyldimethylsilyl)-2-deoxy-2-C-(formylmethyl)-2-C-vinyl-α-D-glucopyranoside

There total 8 articles about Methyl 4,6-O-Benzylidene-3-O-(tert-butyldimethylsilyl)-2-deoxy-2-C-(formylmethyl)-2-C-vinyl-α-D-glucopyranoside 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: 85.0%

: 89872-86-6
Methyl 4,6-O-Benzylidene-3-O-(tert-butyldimethylsilyl)-2-deoxy-2-C-(((vinyloxy)methyl)methylene)-α-D-arabino-hexopyranoside

: 78329-24-5
Methyl 4,6-O-Benzylidene-3-O-(tert-butyldimethylsilyl)-2-deoxy-2-C-(formylmethyl)-2-C-vinyl-α-D-glucopyranoside

Guidance literature:: In benzonitrile; Heating;
DOI:10.1021/jo00187a010

Reference yield:

: 78342-32-2
Methyl 4,6-O-benzylidene-3-O-(t-butyldimethylsilyl)-α-D-ribo-hexopyranosid-2-uloside

: 78329-24-5
Methyl 4,6-O-Benzylidene-3-O-(tert-butyldimethylsilyl)-2-deoxy-2-C-(formylmethyl)-2-C-vinyl-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 90 percent / acetonitrile / Heating

2: 90 percent / LiAlH₄ / diethyl ether / 0.5 h / 0 °C

3: 90 percent / mercuric trifluoroacetate

4: 85 percent / benzonitrile / Heating

With lithium aluminium tetrahydride; mercury(II) trifluoroacetate; In diethyl ether; benzonitrile; acetonitrile;
DOI:10.1021/jo00187a010

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 78329-24-5
Methyl 4,6-O-Benzylidene-3-O-(tert-butyldimethylsilyl)-2-deoxy-2-C-(formylmethyl)-2-C-vinyl-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: Imidazole / dimethylformamide / 4 h / Ambient temperature

2: 90 percent / dimethylsulfoxide, trifluoracetic anhydride / CH₂Cl₂ / 0.5 h / -78 °C

3: 90 percent / acetonitrile / Heating

4: 90 percent / LiAlH₄ / diethyl ether / 0.5 h / 0 °C

5: 90 percent / mercuric trifluoroacetate

6: 85 percent / benzonitrile / Heating

With 1H-imidazole; lithium aluminium tetrahydride; mercury(II) trifluoroacetate; dimethyl sulfoxide; trifluoroacetic anhydride; In diethyl ether; dichloromethane; benzonitrile; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo00187a010