(2R,3S,4R,7S,8R,9R,10R,11S)-2,8-bis-[(tert-butyldimethyl)silyloxy]-3,7,9-trimethyl-4-O-[2,6-deoxy-3,4-bis-O-(tert-butyldimethyl)silyl-β-D-glucopyranosyl]-10-[(benzoyl)oxy]-11-methoxy-13-trimethylsilyl-tridec-4-ol-12-yn-6-one

Base Information

Chemical Name:(2R,3S,4R,7S,8R,9R,10R,11S)-2,8-bis-[(tert-butyldimethyl)silyloxy]-3,7,9-trimethyl-4-O-[2,6-deoxy-3,4-bis-O-(tert-butyldimethyl)silyl-β-D-glucopyranosyl]-10-[(benzoyl)oxy]-11-methoxy-13-trimethylsilyl-tridec-4-ol-12-yn-6-one
CAS No.:749900-27-4
Molecular Formula:C₅₇H₁₀₈O₁₀Si₅
Molecular Weight:1093.91
Hs Code.:

(2R,3S,4R,7S,8R,9R,10R,11S)-2,8-bis-[(tert-butyldimethyl)silyloxy]-3,7,9-trimethyl-4-O-[2,6-deoxy-3,4-bis-O-(tert-butyldimethyl)silyl-β-D-glucopyranosyl]-10-[(benzoyl)oxy]-11-methoxy-13-trimethylsilyl-tridec-4-ol-12-yn-6-one

Synonyms:(2R,3S,4R,7S,8R,9R,10R,11S)-2,8-bis-[(tert-butyldimethyl)silyloxy]-3,7,9-trimethyl-4-O-[2,6-deoxy-3,4-bis-O-(tert-butyldimethyl)silyl-β-D-glucopyranosyl]-10-[(benzoyl)oxy]-11-methoxy-13-trimethylsilyl-tridec-4-ol-12-yn-6-one

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Chemical Property of (2R,3S,4R,7S,8R,9R,10R,11S)-2,8-bis-[(tert-butyldimethyl)silyloxy]-3,7,9-trimethyl-4-O-[2,6-deoxy-3,4-bis-O-(tert-butyldimethyl)silyl-β-D-glucopyranosyl]-10-[(benzoyl)oxy]-11-methoxy-13-trimethylsilyl-tridec-4-ol-12-yn-6-one

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Technology Process of (2R,3S,4R,7S,8R,9R,10R,11S)-2,8-bis-[(tert-butyldimethyl)silyloxy]-3,7,9-trimethyl-4-O-[2,6-deoxy-3,4-bis-O-(tert-butyldimethyl)silyl-β-D-glucopyranosyl]-10-[(benzoyl)oxy]-11-methoxy-13-trimethylsilyl-tridec-4-ol-12-yn-6-one

There total 13 articles about (2R,3S,4R,7S,8R,9R,10R,11S)-2,8-bis-[(tert-butyldimethyl)silyloxy]-3,7,9-trimethyl-4-O-[2,6-deoxy-3,4-bis-O-(tert-butyldimethyl)silyl-β-D-glucopyranosyl]-10-[(benzoyl)oxy]-11-methoxy-13-trimethylsilyl-tridec-4-ol-12-yn-6-one 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: 90.0%

: 493033-95-7
(2R,3S,4R,7S,8R,9R,10R,11S)-2,8-bis-[(tert-butyldimethyl)silyloxy]-3,7,9-trimethyl-4-O-[2'-deoxy-2'-iodo-3',4'-bis-O-(tert-butyldimethyl)silyl-6'-bromo-β-D-glucopyranosyl]-10-[(benzoyl)oxy]-11-methoxy-13-trimethylsilyl-tridec-4-ol-12-yn-6-one

: 749900-27-4
(2R,3S,4R,7S,8R,9R,10R,11S)-2,8-bis-[(tert-butyldimethyl)silyloxy]-3,7,9-trimethyl-4-O-[2,6-deoxy-3,4-bis-O-(tert-butyldimethyl)silyl-β-D-glucopyranosyl]-10-[(benzoyl)oxy]-11-methoxy-13-trimethylsilyl-tridec-4-ol-12-yn-6-one

Guidance literature:: With triethyl borane; tri-n-butyl-tin hydride; In hexane; toluene; at 23 ℃; for 12h;
DOI:10.1021/ja048493l

Reference yield:

: 6-bromo-3,4-bis-O-(tert-butyldimethylsilyl)-2,6-dideoxy-2-iodo-β-D-glucopyranosyl acetate

: 749900-27-4
(2R,3S,4R,7S,8R,9R,10R,11S)-2,8-bis-[(tert-butyldimethyl)silyloxy]-3,7,9-trimethyl-4-O-[2,6-deoxy-3,4-bis-O-(tert-butyldimethyl)silyl-β-D-glucopyranosyl]-10-[(benzoyl)oxy]-11-methoxy-13-trimethylsilyl-tridec-4-ol-12-yn-6-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: hydrazine / methanol; diethyl ether; H₂O / 1.5 h / 0 °C

1.2: 78 percent / diethylaminosulfur trifluoride / CH₂Cl₂ / 0.5 h / 0 °C

2.1: 84 percent / SnCl₂; AgClO₄ / diethyl ether / 0.5 h / -15 °C

3.1: 90 percent / Bu₃SnH; triethylborane / toluene; hexane / 12 h / 23 °C

With triethyl borane; tri-n-butyl-tin hydride; silver perchlorate; tin(ll) chloride; hydrazine; In methanol; diethyl ether; hexane; water; toluene;
DOI:10.1021/ja048493l

Reference yield:

: 251301-00-5
(2R,3S)-3-[(-O-tert-Butyldimethylsilyl)oxy]-2-methylbutan-1-ol

: 749900-27-4
(2R,3S,4R,7S,8R,9R,10R,11S)-2,8-bis-[(tert-butyldimethyl)silyloxy]-3,7,9-trimethyl-4-O-[2,6-deoxy-3,4-bis-O-(tert-butyldimethyl)silyl-β-D-glucopyranosyl]-10-[(benzoyl)oxy]-11-methoxy-13-trimethylsilyl-tridec-4-ol-12-yn-6-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 61 mg / pyridine; Dess-Martin periodinane; H₂O / CH₂Cl₂ / 23 °C

2.1: TMSCl; Et₃N; LiHMDS / tetrahydrofuran / 1 h / -78 °C

2.2: 66 percent / BF₃*OEt₂ / CH₂Cl₂ / 1 h / -78 °C

3.1: 84 percent / SnCl₂; AgClO₄ / diethyl ether / 0.5 h / -15 °C

4.1: 90 percent / Bu₃SnH; triethylborane / toluene; hexane / 12 h / 23 °C

With pyridine; chloro-trimethyl-silane; triethyl borane; water; tri-n-butyl-tin hydride; silver perchlorate; Dess-Martin periodane; triethylamine; tin(ll) chloride; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; 1.1: Dess-Martin oxidation / 2.2: Mukaiyama aldol coupling;
DOI:10.1021/ja048493l