950599-08-3

Basic information

• Product Name: (2R,3S,4R,5R,6R)-2-allyl-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidine
• Synonyms: (2R,3S,4R,5R,6R)-2-allyl-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidine
• CAS NO: 950599-08-3
• Molecular Weight: 563.737
• Mol File: 950599-08-3.mol

Chemical Properties

• CAS DataBase Reference: (2R,3S,4R,5R,6R)-2-allyl-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidine(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S,4R,5R,6R)-2-allyl-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidine(950599-08-3)
• EPA Substance Registry System: (2R,3S,4R,5R,6R)-2-allyl-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidine(950599-08-3)

Safety Data

• Hazardous Substances Data: 950599-08-3(Hazardous Substances Data)

Upstream product

• 1222826-97-2 (1R)-2,3,4,6-tetra-O-benzyl-N-[(4-methoxybenzyl)amino]-1-C-(prop-2-enyl)-1-deoxynojirimycin 
• 24850-33-7 allyltributylstanane 
• 77174-08-4 (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidin-2-one 
• 292062-92-1 (3R,4R,5S,6R)-6-[N-benzyl-N-(fluoren-9-ylmethoxycarbonyl)amino]-1,3,4,5-tetrakis(benzyloxy)non-8-en-2-one 
• 1054633-26-9 (3S,4R,5S,6R)-6-Benzylamino-1,3,4,5-tetrakis-benzyloxy-non-8-en-2-one 
• 166111-63-3 N-benzyl-2,3,4,6-tetra-O-benzyl-D-glucopyranosylamine 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 292062-93-2 (2R,3R,4R,5S,6R)-N-benzyl-3,4,5-tris(benzyloxy)-2-benzyloxymethyl-6-(prop-2-enyl)piperidine 

Downstream Products

• 1054653-75-6 (2R,3R,4R,5S,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(2-oxo-ethyl)-piperidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester 
• 497931-28-9 (2R,3R,4R,5S,6R)-3,4,5-tris(benzyloxy)-2-benzyloxymethyl-N-(fluoren-9-ylmethoxycarbonyl)-6-(prop-2-enyl)piperidine 

Relevant articles and documents

Concise synthesis of bicyclic iminosugarsviareductive functionalization of sugar-derived lactams and subsequent RCM reaction

An efficient method for the synthesis of bicyclic iminosugars has been developed. The strategy is based on the partial reduction of sugar-derived lactams by Schwartz's reagent and tandem stereoselective nucleophile addition dictated by Woerpel's model which affords polyhydroxylated cyclic amines as key intermediates. Introduction of a vinyl or allyl group to the iminosugar produces diene derivatives that can be subjected to the ring-closing metathesis reaction (RCM) to furnish polyhydroxylated pyrrolizidine, indolizidine and quinozilidine derivatives in good to excellent yields. This sequence of reactions has been applied to the formal synthesis of hyacinthacine A2, a polyhydroxylated pyrrolizidine alkaloid.

Sugar-derived cyclic imines: One-pot synthesis and direct functionalization

A simple method for the synthesis of sugar-derived imines by a Schwartz's reagent reduction of easily available sugar lactams has been described. A direct addition of nucleophiles to the generated in situ cyclic imines and subsequent deprotection of hydroxyl function allows to convert sugar lactams in polyhydroxylated pyrrolidines and piperidines.

Synthesis and evaluation of lipophilic Aza-C-glycosides as inhibitors of glucosylceramide metabolism

The structure-activity relationship of lipophilic aza-C-glycosides as inhibitors of the three enzymes of glucosylceramide metabolism is investigated. A library of β-aza-C-glycosides was synthesized with variations in N-alkylation and the linker length/typ

Synthesis of nojirimycin C-glycosides

Nojirimycin α-C-glycosides, which have 1-α-allyl-1-deoxy-N-benzyl-2,3,4,6-tetra-O-benzylnojirimycin (9) as a key intermediate for further derivatisation, have been synthesized from commercially available 2,3,4,6-tetra-O-benzyl-D-glucopyranose (3) through a highly stereoselective procedure which involves treatment of 3 with benzylamine, reaction of the obtained glucosylamine 4 with allylmagnesium bromide and cyclization of the elongated open-chain aminosugar 5 by Fmoc-protection, oxidation of the free hydroxy group, and intramolecular reductive-amination, affording 9 in 59% overall yield. The efficient manipulation of the allylic appendage of 9 has required N-debenzylation and Fmoc-protection of the ring-nitrogen.