656827-11-1

Basic information

• Product Name: Carbamic acid, [(4S,5R)-2,2-dimethyl-4-(2-propenyl)-1,3-dioxan-5-yl]-, phenylmethyl ester
• CAS NO: 656827-11-1
• Molecular Formula: C17H23NO4
• Molecular Weight: 305.374
• Mol File: 656827-11-1.mol

Chemical Properties

• CAS DataBase Reference: Carbamic acid, [(4S,5R)-2,2-dimethyl-4-(2-propenyl)-1,3-dioxan-5-yl]-, phenylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [(4S,5R)-2,2-dimethyl-4-(2-propenyl)-1,3-dioxan-5-yl]-, phenylmethyl ester(656827-11-1)
• EPA Substance Registry System: Carbamic acid, [(4S,5R)-2,2-dimethyl-4-(2-propenyl)-1,3-dioxan-5-yl]-, phenylmethyl ester(656827-11-1)

Safety Data

• Hazardous Substances Data: 656827-11-1(Hazardous Substances Data)

Upstream product

• 77-76-9 2,2-dimethoxy-propane 
• 656827-17-7 (2R,3S)-2-(benzyloxycarbonyl)amino-hex-5-ene-1,3-diol 
• 6081-61-4 N-(benzyloxycarbonyl)-D-serine 
• 1092473-80-7 (R)-benzyl 3-hydroxy-1-(methoxy(methyl)amino)-1-oxopropane-2-ylcarbamate 
• 656827-13-3 (R)-benzyl-4-(methoxy(methyl)carbamoyl)-2,2-dimethyloxazolidine-3-carboxylate 
• 656827-14-4 1-[(4R)-3-N-benzyloxycarbonyl-2,2-dimethyl-1,3-oxazolidin-4-yl]-but-3-en-1-one 
• 656827-16-6 (1S)-1-[(4R)-3-N-benzyloxycarbonyl-2,2-dimethyl-1,3-oxazolidin-4-yl]-but-3-en-1-ol 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 656827-17-7 (2R,3S)-2-(benzyloxycarbonyl)amino-hex-5-ene-1,3-diol 
• 1450984-49-2 benzyl (2R,3S,5S)-3-hydroxy-2-hydroxymethyl-5-(iodomethyl)pyrrolidine-1-carboxylate 
• 1450984-51-6 C₁₈H₂₂INO₆ 
• 656827-21-3 methyl (4aR,6S,7aS)-5-benzyloxycarbonyl-2,2-dimethylhexahydro[1,3]dioxino[5,4-b]pyrrol-6-carboxylate 
• 656827-19-9 (4aR,6S,7aS)-benzyl 6-hydroxymethyl-2,2-dimethyltetrahydro[1,3]dioxino[5,4-b]pyrrole-5(6H)-carboxylate 

Relevant articles and documents

Polyhydroxylated pyrrolidine and 2-oxapyrrolizidine as glycosidase inhibitors

Using D-serine as a chiral precursor, a polyhydroxylated pyrrolidine (1), its derivatives bearing carboxylate, phosphate and phosphonate groups (2-4) and an oxapyrrolizidine (5) were synthesized. The pyrrolidine ring was formed by intramolecular amino-mercuration. The bicyclic scaffold of oxapyrrolizidine was further constructed by an intramolecular attack of the carbamate group on the iodomethyl group. Compounds 1 and 5 were found to inhibit β-glucosidase and α-galactosidase, respectively, in a competitive manner, whereas compounds 2, 3 and 4 did not produce significant inhibition against glycosidases. The Royal Society of Chemistry 2013.

D-glucosamine-derived synthons for assembly of l - Threo -sphingoid bases. Total synthesis of rhizochalinin C

A five-step transformation of d-glucosamine, commencing with indium-mediated Barbier reaction without isolation of intermediates, into (R,R)-2-aminohex-5-ene-1,3-diol in 45-51% is described. The latter is a useful synthon for assembly of l-threo-sphingoid bases: long-chain aminoalkanols and aminoalkanediols with configurations antipodal to that found in mammalian D-erythro-sphingosine but prevalent among invertebrate-derived sphingolipids. The utility of the method is demonstrated by the first total synthesis of rhizochalinin C, the long-chain, two-headed sphingoid base aglycon of the natural product rhizochalin C from the marine sponge Rhizochalina incrustata.

An Efficient and Highly Stereocontrolled Route to Bulgecinine Hydrochloride

(-)-Bulgecinine is a nonproteinogenic amino acid component present in bulgecins A, B, and C, antibiotic glycopeptides derived from Pseudomonas acidophila and Pseudomonas mesoacidophila. In combination with β-lactam antibiotics, bulgecins exihibit a unique