methyl 2,3,5-tri-O-tert-butyldimethylsilyl-6-S-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-6-thio-β-D-galactofuranoside

Base Information

Chemical Name:methyl 2,3,5-tri-O-tert-butyldimethylsilyl-6-S-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-6-thio-β-D-galactofuranoside
CAS No.:1435894-99-7
Molecular Formula:C₅₉H₈₂O₁₄SSi₃
Molecular Weight:1131.61
Hs Code.:

Synonyms:methyl 2,3,5-tri-O-tert-butyldimethylsilyl-6-S-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-6-thio-β-D-galactofuranoside

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Chemical Property of methyl 2,3,5-tri-O-tert-butyldimethylsilyl-6-S-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-6-thio-β-D-galactofuranoside

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Technology Process of methyl 2,3,5-tri-O-tert-butyldimethylsilyl-6-S-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-6-thio-β-D-galactofuranoside

There total 6 articles about methyl 2,3,5-tri-O-tert-butyldimethylsilyl-6-S-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-6-thio-β-D-galactofuranoside 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: 61.0%

: 1435894-98-6
methyl 2,3,5-tri-O-tert-butyldimethylsilyl-6-thio-β-D-galactofuranoside

: 226211-26-3
O-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-trichloroacetimidate

: 1435894-99-7
methyl 2,3,5-tri-O-tert-butyldimethylsilyl-6-S-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-6-thio-β-D-galactofuranoside

Guidance literature:: methyl 2,3,5-tri-O-tert-butyldimethylsilyl-6-thio-β-D-galactofuranoside; O-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-trichloroacetimidate; With methyl 2,3,5-tri-O-(tert-butyldimethylsilyl)-β-D-galactofuranoside; In dichloromethane; at 20 ℃; for 1.5h; Molecular sieve;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -18 ℃; for 0.666667h;

With triethylamine; In dichloromethane; at -18 ℃;
DOI:10.1016/j.bmc.2013.02.057

Reference yield:

: methyl (methyl 2,3,5-tri-O-tert-butyldimethylsilyl-α,β-D-galactofuranosid)uronate

: 1435894-99-7
methyl 2,3,5-tri-O-tert-butyldimethylsilyl-6-S-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-6-thio-β-D-galactofuranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / -18 °C

1.2: pH 7

2.1: 2,6-di-tert-butyl-4-methylpyridine / dichloromethane / 1 h / 0 °C / Inert atmosphere

3.1: acetonitrile / 3 h / 0 °C

4.1: sodium methylate; methanol / dichloromethane / 2 h / -15 °C

5.1: methyl 2,3,5-tri-O-(tert-butyldimethylsilyl)-β-D-galactofuranoside / dichloromethane / 1.5 h / 20 °C / Molecular sieve

5.2: 0.67 h / -18 °C

5.3: -18 °C

With methanol; lithium aluminium tetrahydride; 2,6-di-tert-butyl-4-methylpyridine; methyl 2,3,5-tri-O-(tert-butyldimethylsilyl)-β-D-galactofuranoside; sodium methylate; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1016/j.bmc.2013.02.057

Reference yield:

: 1351685-98-7
methyl 2,3,5-tri-O-(tert-butyldimethylsilyl)-β-D-galactofuranoside

: 1435894-99-7
methyl 2,3,5-tri-O-tert-butyldimethylsilyl-6-S-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-6-thio-β-D-galactofuranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: 2,6-di-tert-butyl-4-methylpyridine / dichloromethane / 1 h / 0 °C / Inert atmosphere

2.1: acetonitrile / 3 h / 0 °C

3.1: sodium methylate; methanol / dichloromethane / 2 h / -15 °C

4.1: methyl 2,3,5-tri-O-(tert-butyldimethylsilyl)-β-D-galactofuranoside / dichloromethane / 1.5 h / 20 °C / Molecular sieve

4.2: 0.67 h / -18 °C

4.3: -18 °C

With methanol; 2,6-di-tert-butyl-4-methylpyridine; methyl 2,3,5-tri-O-(tert-butyldimethylsilyl)-β-D-galactofuranoside; sodium methylate; In dichloromethane; acetonitrile;
DOI:10.1016/j.bmc.2013.02.057