(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

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'-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
CAS No.:493033-95-7
Molecular Formula:C₅₇H₁₀₆BrIO₁₀Si₅
Molecular Weight:1298.7
Hs Code.:

(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

Synonyms:(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

Suppliers and Price of (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

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 0 raw suppliers

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of (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

There total 11 articles about (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 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: 84.0%

: 493033-92-4
6-bromo-3,4-bis-O-(tert-butyldimethylsilyl)-2,6-dideoxy-2-iodo-β-D-glucopyranosyl fluoride

: 493033-94-6
(2R,3S,4R,7S,8R,9R,10R,11S)-2,8-di-[(tert-butyldimethyl)silyloxy]-3,7,9-trimethyl-10-[(benzoyl)oxy]-11-methoxy-13-trimethylsilyl-tridec-4-ol-12-yn-6-one

: 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

Guidance literature:: With silver perchlorate; tin(ll) chloride; In diethyl ether; at -15 ℃; for 0.5h;
DOI:10.1021/ja048493l

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 2 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

With silver perchlorate; tin(ll) chloride; hydrazine; In methanol; diethyl ether; water;
DOI:10.1021/ja048493l

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 3 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

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