methyl 4,6-O-benzylidene-3-O-t-butyldimethylsilyl-2-deoxy-2-C-(prop-2-enyl)-α-D-altroside

Base Information

Chemical Name:methyl 4,6-O-benzylidene-3-O-t-butyldimethylsilyl-2-deoxy-2-C-(prop-2-enyl)-α-D-altroside
CAS No.:131529-57-2
Molecular Formula:C₂₃H₃₆O₅Si
Molecular Weight:420.621
Hs Code.:

Synonyms:methyl 4,6-O-benzylidene-3-O-t-butyldimethylsilyl-2-deoxy-2-C-(prop-2-enyl)-α-D-altroside

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Chemical Property of methyl 4,6-O-benzylidene-3-O-t-butyldimethylsilyl-2-deoxy-2-C-(prop-2-enyl)-α-D-altroside

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Technology Process of methyl 4,6-O-benzylidene-3-O-t-butyldimethylsilyl-2-deoxy-2-C-(prop-2-enyl)-α-D-altroside

There total 2 articles about methyl 4,6-O-benzylidene-3-O-t-butyldimethylsilyl-2-deoxy-2-C-(prop-2-enyl)-α-D-altroside 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: 95.0%

: 126108-10-9
methyl 4,6-O-benzylidene-2-deoxy-2-(2-propenyl)-α-D-allohexopyranoside

: 18162-48-6
tert-butyldimethylsilyl chloride

: 131529-57-2
methyl 4,6-O-benzylidene-3-O-t-butyldimethylsilyl-2-deoxy-2-C-(prop-2-enyl)-α-D-altroside

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 80 ℃; for 22h;
DOI:10.1071/CH9901681

Reference yield:

: 66537-92-6
methyl 2,3-anhydro-4,6-benzylidene-α-D-allopyranoside

: 131529-57-2
methyl 4,6-O-benzylidene-3-O-t-butyldimethylsilyl-2-deoxy-2-C-(prop-2-enyl)-α-D-altroside

Guidance literature:: Multi-step reaction with 2 steps

1: 97 percent / allylmagnesium chloride / tetrahydrofuran / 2 h

2: 95 percent / imidazole / dimethylformamide / 22 h / 80 °C

With 1H-imidazole; allylmagnesium bromide; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1071/CH9901681

Reference yield:

: 131529-57-2
methyl 4,6-O-benzylidene-3-O-t-butyldimethylsilyl-2-deoxy-2-C-(prop-2-enyl)-α-D-altroside

: 131529-64-1
methyl 3-O-benzoyl-4-O-t-butyldimethylsilyl-6-cyano-2,6-dideoxy-2-C-(2-methoxycarbonylethyl)-α-D-altroside

Guidance literature:: Multi-step reaction with 7 steps

2: 300 mg / pyridinium dichromate / dimethylformamide / 23 h

3: diethyl ether

4: 83 percent / N-bromosuccinimide, barium carbonate / CCl₄ / 20 h / Heating

5: 82 percent / hexamethylphosphoric acid triamide / 48 h

6: 36 percent / sodium methoxide / methanol / 26 h

7: 24 h

With N-Bromosuccinimide; dipyridinium dichromate; sodium methylate; barium carbonate; In methanol; tetrachloromethane; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; N,N-dimethyl-formamide;
DOI:10.1071/CH9901681