methyl 4,6-O-benzylidene-2-C-(2-(tert-butyldimethylsiloxy)ethyl)-2,3-dideoxy-3-C-(2-oxopropyl)-3-C-vinyl-α-D-allopyranoside

Base Information

Chemical Name:methyl 4,6-O-benzylidene-2-C-(2-(tert-butyldimethylsiloxy)ethyl)-2,3-dideoxy-3-C-(2-oxopropyl)-3-C-vinyl-α-D-allopyranoside
CAS No.:122950-07-6
Molecular Formula:C₂₇H₄₂O₆Si
Molecular Weight:490.712
Hs Code.:

Synonyms:methyl 4,6-O-benzylidene-2-C-(2-(tert-butyldimethylsiloxy)ethyl)-2,3-dideoxy-3-C-(2-oxopropyl)-3-C-vinyl-α-D-allopyranoside

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Chemical Property of methyl 4,6-O-benzylidene-2-C-(2-(tert-butyldimethylsiloxy)ethyl)-2,3-dideoxy-3-C-(2-oxopropyl)-3-C-vinyl-α-D-allopyranoside

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Technology Process of methyl 4,6-O-benzylidene-2-C-(2-(tert-butyldimethylsiloxy)ethyl)-2,3-dideoxy-3-C-(2-oxopropyl)-3-C-vinyl-α-D-allopyranoside

There total 8 articles about methyl 4,6-O-benzylidene-2-C-(2-(tert-butyldimethylsiloxy)ethyl)-2,3-dideoxy-3-C-(2-oxopropyl)-3-C-vinyl-α-D-allopyranoside 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: 89.0%

: 917-54-4
methyllithium

: methyl 4,6-O-benzylidene-2-C-(2-(tert-butyldimethylsiloxy)ethyl)-2,3-dideoxy-3-C-((N,N-dimethylcarbamoyl)methyl)-3-C-vinyl-α-D-allopyranoside

: 122950-07-6
methyl 4,6-O-benzylidene-2-C-(2-(tert-butyldimethylsiloxy)ethyl)-2,3-dideoxy-3-C-(2-oxopropyl)-3-C-vinyl-α-D-allopyranoside

Guidance literature:: In diethyl ether; at -78 ℃; for 0.166667h;
DOI:10.1021/jo00283a033

Reference yield:

: 122672-65-5
methyl 2-deoxy-2-(2-ethoxy-2-oxoethyl)-4,6-O-(phenylmethylene)-α-D-ribohexopyranosid-3-ulose

: 122950-07-6
methyl 4,6-O-benzylidene-2-C-(2-(tert-butyldimethylsiloxy)ethyl)-2,3-dideoxy-3-C-(2-oxopropyl)-3-C-vinyl-α-D-allopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 98 percent / acetonitrile / 72 h / Heating

2: 71 percent / DIBAL / CH₂Cl₂

3: 68 percent / molecular sieves 4A / toluene / 10 h

4: 81 percent / imidazole / tetrahydrofuran / 1 h / Ambient temperature

5: 89 percent / diethyl ether / 0.17 h / -78 °C

With 1H-imidazole; 4 A molecular sieve; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; acetonitrile;
DOI:10.1021/jo00283a033

Reference yield:

: 194149-26-3
methyl 2,3:4,6-di-O-benzylidene-α-D-mannopyranoside

: 122950-07-6
methyl 4,6-O-benzylidene-2-C-(2-(tert-butyldimethylsiloxy)ethyl)-2,3-dideoxy-3-C-(2-oxopropyl)-3-C-vinyl-α-D-allopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) n-BuLi, 2.) hexamethylphosphoramide / 1.) THF, from -40 deg C to -30 deg C, 30 min, 2.) THF, from -35 deg C to -30 deg C

2: 98 percent / acetonitrile / 72 h / Heating

3: 71 percent / DIBAL / CH₂Cl₂

4: 68 percent / molecular sieves 4A / toluene / 10 h

5: 81 percent / imidazole / tetrahydrofuran / 1 h / Ambient temperature

6: 89 percent / diethyl ether / 0.17 h / -78 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; 4 A molecular sieve; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; acetonitrile;
DOI:10.1021/jo00283a033