2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-3,4-di-O-benzyl-6-O-tert-butyldimethylsilyl-β-D-glucopyranosyl fluoride

Base Information

Chemical Name:2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-3,4-di-O-benzyl-6-O-tert-butyldimethylsilyl-β-D-glucopyranosyl fluoride
CAS No.:313948-45-7
Molecular Formula:C₆₀H₇₁FO₁₀Si
Molecular Weight:999.302
Hs Code.:

Synonyms:2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-3,4-di-O-benzyl-6-O-tert-butyldimethylsilyl-β-D-glucopyranosyl fluoride

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Chemical Property of 2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-3,4-di-O-benzyl-6-O-tert-butyldimethylsilyl-β-D-glucopyranosyl fluoride

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Technology Process of 2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-3,4-di-O-benzyl-6-O-tert-butyldimethylsilyl-β-D-glucopyranosyl fluoride

There total 3 articles about 2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-3,4-di-O-benzyl-6-O-tert-butyldimethylsilyl-β-D-glucopyranosyl fluoride 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: 86.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 313948-55-9
2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-3,4-di-O-benzyl-β-D-glucopyranosyl fluoride

: 313948-45-7
2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-3,4-di-O-benzyl-6-O-tert-butyldimethylsilyl-β-D-glucopyranosyl fluoride

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 5h;
DOI:10.1016/S0040-4020(00)00793-6

Reference yield:

: [(2R,3R,4S,5R,6S)-3,4-Bis-benzyloxy-6-fluoro-5-((3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethoxy]-tert-butyl-dimethyl-silane

: 313948-45-7
2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-3,4-di-O-benzyl-6-O-tert-butyldimethylsilyl-β-D-glucopyranosyl fluoride

Guidance literature:: Multi-step reaction with 2 steps

1: 59 percent / n-Bu₄NF / tetrahydrofuran / 23 h / 20 °C

2: 86 percent / imidazole / dimethylformamide / 5 h / 20 °C

With 1H-imidazole; tetrabutyl ammonium fluoride; In tetrahydrofuran; N,N-dimethyl-formamide; 1: desilylation / 2: silylation;
DOI:10.1016/S0040-4020(00)00793-6

Reference yield:

: 105990-37-2
ethyl-2,3,4,6-tetra-O-benzyl-1-thio-D-glucopyranose

: 313948-46-8
3,4-di-O-benzyl-6-O-tert-butyldimethylsilyl-β-D-glucopyranosyl fluoride

: 313948-45-7
2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-3,4-di-O-benzyl-6-O-tert-butyldimethylsilyl-β-D-glucopyranosyl fluoride

: [(2R,3R,4S,5R,6S)-3,4-Bis-benzyloxy-6-fluoro-5-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethoxy]-tert-butyl-dimethyl-silane

Guidance literature:: With N-iodo-succinimide; lithium perchlorate; In diethyl ether; Further Variations:; Solvents; Reagents; Product distribution;
DOI:10.1016/S0040-4020(00)00793-6