102487-51-4

Basic information

• Product Name: Benzoic acid (4R,5R)-5-[(R)-(tert-butyl-dimethyl-silanyloxy)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester
• CAS NO: 102487-51-4
• Molecular Weight: 480.674
• Mol File: 102487-51-4.mol

Chemical Properties

• CAS DataBase Reference: Benzoic acid (4R,5R)-5-[(R)-(tert-butyl-dimethyl-silanyloxy)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid (4R,5R)-5-[(R)-(tert-butyl-dimethyl-silanyloxy)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester(102487-51-4)
• EPA Substance Registry System: Benzoic acid (4R,5R)-5-[(R)-(tert-butyl-dimethyl-silanyloxy)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester(102487-51-4)

Safety Data

• Hazardous Substances Data: 102487-51-4(Hazardous Substances Data)

Upstream product

• 7115-22-2 1-O-benzoyl-2,3:5,6-di-O-isopropylidene-D-mannitol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 3969-61-7 2,3,5,6-di-isopropyIidene-1,4-dihydroxy-D-mannitol 
• 98-88-4 benzoyl chloride 
• 69739-34-0 t-butyldimethylsiyl triflate 

Downstream Products

• 102487-65-0 (S)-3-{(2S,3R)-3-[(4R,5S)-5-(Benzyloxycarbonylamino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxiranyl}-3-hydroxy-propionic acid tert-butyl ester 
• 102487-62-7 (R)-3-{(2S,3R)-3-[(4R,5S)-5-(Benzyloxycarbonylamino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxiranyl}-3-hydroxy-propionic acid tert-butyl ester 
• 102487-62-7 3-{(2S,3R)-3-[(4R,5S)-5-(Benzyloxycarbonylamino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxiranyl}-3-hydroxy-propionic acid tert-butyl ester 
• 102487-63-8 3-{(2R,3R)-3-[(4R,5S)-5-(Benzyloxycarbonylamino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxiranyl}-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid tert-butyl ester 
• 102487-56-9 {(4S,5R)-5-[(R)-(tert-Butyl-dimethyl-silanyloxy)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl}-carbamic acid benzyl ester 
• 102487-59-2 Methanesulfonic acid (2R,3R)-3-[(4S,5S)-5-(benzyloxycarbonylamino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2,3-dihydroxy-propyl ester 
• 102487-57-0 {(4S,5R)-5-[(1R,2R)-1-(tert-Butyl-dimethyl-silanyloxy)-2,3-dihydroxy-propyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl}-carbamic acid benzyl ester 
• 102487-58-1 [(4S,5S)-2,2-Dimethyl-5-((1R,2R)-1,2,3-trihydroxy-propyl)-[1,3]dioxolan-4-ylmethyl]-carbamic acid benzyl ester 
• 102487-60-5 [(4S,5S)-5-((R)-Hydroxy-(R)-oxiranyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl]-carbamic acid benzyl ester 
• 102518-70-7 [(4S,5R)-5-((2R,3S)-3-Hydroxymethyl-oxiranyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl]-carbamic acid benzyl ester 
• 102487-61-6 [(4S,5R)-5-((2S,3R)-3-Formyl-oxiranyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl]-carbamic acid benzyl ester 
• 89955-60-2 1-epi-castanospermine 
• 79831-76-8 (1S,6S,7R,8R,8aR)-2,6,7,8-tetrahydroxy-indolizidine 

Relevant articles and documents

The Baylis-Hillman reaction: a strategic tool for the synthesis of higher-carbon sugars

The Baylis-Hillman reaction of acyclic sugar-derived aldehydes is invoked as an attractive synthetic strategy for ready access to higher-carbon sugars.

Condensation of D-mannosaldehyde derivatives with ethyl diazoacetate. An easy and stereoselective chain elongation methodology for carbohydrates: Application to new syntheses for KDO and 2-deoxy-β-KDO

(3R and 3S) β-Hydroxy-α-diazocarbonyl compounds 4 (100%, 3:2), 9 (35%, 100:0), 14 (74%, 7:2) and 18 (100%, 100:0), prepared from 2,3,4,5,6-penta-O-acetyl-(3), penta-O-benzyl- (8), 2,3:5,6-di-O-isopropylidene-4-O-(tert-butyldimethylsilyl)- (13), and 2,3:5,6-di-O-isopropylidene-4-O-acetyl-D-mannosaldehyde (17), respectively, were acetylated, and the resulting β-3cetoxy-α-diazocarbonyl compounds treated with rhodium diacetate to give the corresponding α-enol esters, 6 (100%). 11 (35%), 16 (100%) and 20 (100%) which are potentially α-keto eaters. Molecular mechanics calculations were used in order to justify the stereoselectivity observed in the initial addition process: The problematic removal of the projecting groups from the α-enol esters is discussed. Finally, hydrazinolysis of the a-enol acetates (to quench the labile resulting α-keto ester as the corresponding and less reactive hydrazines), mild oxidation to the corresponding α-diazoesters, deprotection, and final oxidation of the diazo group with m-chloroperbenzoic acid, gave KDO in good yield. Intermediate products were used in the completely stereoselective synthesis of 2-deoxy-β-KDO, a potent inhibitor for CMP-KDO synthetase.

TOTAL SYNTHESIS OF (+)-CASTANOSPERMINE FROM D-MANNOSE

A total synthesis of (+)-castanospermine (2) has been achieved starting from D-mannose by a route adopting a double-cyclization process (5c-6) as the key step.