331456-83-8

Basic information

• Product Name: S-phenyl 2,3-O-isopropylidene-4-O-(tert-butyldimethylsilyl)-1-thio-α-L-rhamnopyranoside
• Synonyms: S-phenyl 2,3-O-isopropylidene-4-O-(tert-butyldimethylsilyl)-1-thio-α-L-rhamnopyranoside
• CAS NO: 331456-83-8
• Molecular Weight: 410.65
• Mol File: 331456-83-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: S-phenyl 2,3-O-isopropylidene-4-O-(tert-butyldimethylsilyl)-1-thio-α-L-rhamnopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: S-phenyl 2,3-O-isopropylidene-4-O-(tert-butyldimethylsilyl)-1-thio-α-L-rhamnopyranoside(331456-83-8)
• EPA Substance Registry System: S-phenyl 2,3-O-isopropylidene-4-O-(tert-butyldimethylsilyl)-1-thio-α-L-rhamnopyranoside(331456-83-8)

Safety Data

• Hazardous Substances Data: 331456-83-8(Hazardous Substances Data)

Upstream product

• 153745-68-7 phenyl 1-thio-L-rhamnopyranoside 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 77-76-9 2,2-dimethoxy-propane 
• 131087-35-9 phenyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 1214-98-8 phenyl 1-thio-α-L-rhamnopyranose 

Downstream Products

• 400738-33-2 (2S,3S,4R,5S,6S)-2-Benzyloxy-5-[(2S,3R,4S,5R,6R)-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-6-methyl-3-phenylsulfanyl-tetrahydro-pyran-2-yloxy]-4,6-dimethyl-3-phenylsulfanyl-4-triethylsilanyloxy-tetrahydro-pyran 
• 400738-29-6 (2S,3S,4R,5S,6S)-2-Benzyloxy-5-[(2S,3R,4S,5R,6R)-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-6-methyl-3-phenylsulfanyl-tetrahydro-pyran-2-yloxy]-4,6-dimethyl-3-phenylsulfanyl-tetrahydro-pyran-4-ol 
• 400738-00-3 (2S,3S,4S,5R,6S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2,4-dimethyl-6-phenylsulfanyl-tetrahydro-pyran 
• 400738-11-6 (2S,3S,4R,5S,6S)-2-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-3-phenylsulfanyl-tetrahydro-pyran 
• 400738-03-6 (2S,3R,4S,5S,6S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-2-phenylsulfanyl-tetrahydro-pyran-3-ol 
• 400738-14-9 (2S,3S,4R,5S,6S)-6-Benzyloxy-2,4-dimethyl-5-phenylsulfanyl-tetrahydro-pyran-3,4-diol 
• 403646-68-4 4-(4-nitrophenyl)butyl 4,6-O-benzylidene-2-O-pivaloyl-3-O-[4-O-(4,6-O-benzylidene-2,3-di-O-(p-methoxybenzyl)-β-D-mannopyranosyl)-2,3-O-isopropylidene-α-L-rhamnopyranosyl]-β-D-galactopyranoside 
• 403646-61-7 4-(4-nitrophenyl)butyl 4,6-O-benzylidene-2-O-pivaloyl-3-O-(2,3-O-isopropylidene-α-L-rhamnopyranosyl)-β-D-galactopyranoside 
• 400737-85-1 [(2S,3S,4S,5R,6S)-4-Allyloxy-5-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane 
• 400737-98-6 (2S,3S,4S,5R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2,4-dimethyl-6-phenylsulfanyl-tetrahydro-pyran-4-ol 
• 400737-89-5 (2S,3R,4S,5R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-ol 
• 400737-93-1 (2S,3S,5R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-one 
• 400737-82-8 (2S,3R,4S,5S,6S)-4-Allyloxy-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3-ol 
• 403646-59-3 4-(4-nitrophenyl)butyl 4,6-O-benzylidene-2-O-pivaloyl-3-O-(2,3-O-isopropylidene-4-O-(tert-butyldimethylsilyl)-α-L-rhamnopyranosyl)-β-D-galactopyranoside 

Relevant articles and documents

Synthesis of Cardiotonic Steroids Oleandrigenin and Rhodexin B

This article describes a concise synthesis of cardiotonic steroids oleandrigenin (7) and its subsequent elaboration into the natural product rhodexin B (2) from the readily available intermediate (8) that could be derived from the commercially available steroids testosterone or DHEA via three-step sequences. These studies feature an expedient installation of the β16-oxidation based on β14-hydroxyl-directed epoxidation and subsequent epoxide rearrangement. The following singlet oxygen oxidation of the C17 furan moiety provides access to oleandrigenin (7) in 12 steps (LLS) and a 3.1% overall yield from 8. The synthetic oleandrigenin (7) was successfully glycosylated with l-rhamnopyranoside-based donor 28 using a Pd(II)-catalyst, and the subsequent deprotection under acidic conditions provided cytotoxic natural product rhodexin B (2) in a 66% yield (two steps).

Synthesis of the Salmonella type E(1) core trisaccharide as a probe for the generality of 1-(benzenesulfinyl)piperidine/triflic anhydride combination for glycosidic bond formation from thioglycosides.

A synthesis of a chromogenic glycoside of the Salmonella anatum group E(1) core trisaccharide is presented in which all three glycosidic bonds, a 1,2-cis-equatorial, a 1,2-trans-axial, and a 1,2-trans-equatorial linkage representing three of the four main classes of glycosidic bond, are formed with thioglycoside donors activated under a single set of conditions by the combination of 1-(benzenesulfinyl)piperidine and trifluoromethanesulfonic anhydride. 2,3-O-Carbonyl- and 2,3-O-isopropylidene-alpha-L-rhamnopyranosyl thioglycosides are found to be highly alpha-selective rhamnosyl donors under these conditions.

Total synthesis of apoptolidin: Part 1. Retrosynthetic analysis and construction of building blocks

No less than 30 stereogenic elements, a highly unsaturated 20-membered macrocyclic system, four carbohydrate units, and unique biological activity, make the natural occurring apoptolidin (1) a challenging synthetic target. The retrosynthetic analysis reve