505085-04-1

Basic information

• Product Name: (5-benzyloxy-1-benzyloxymethyl-4-tert-butoxycarbonylamino-2,3-dihydroxy-pentyl)-carbamic acid tert-butyl ester
• Synonyms: (5-benzyloxy-1-benzyloxymethyl-4-tert-butoxycarbonylamino-2,3-dihydroxy-pentyl)-carbamic acid tert-butyl ester
• CAS NO: 505085-04-1
• Molecular Weight: 560.688
• Mol File: 505085-04-1.mol

Chemical Properties

• CAS DataBase Reference: (5-benzyloxy-1-benzyloxymethyl-4-tert-butoxycarbonylamino-2,3-dihydroxy-pentyl)-carbamic acid tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (5-benzyloxy-1-benzyloxymethyl-4-tert-butoxycarbonylamino-2,3-dihydroxy-pentyl)-carbamic acid tert-butyl ester(505085-04-1)
• EPA Substance Registry System: (5-benzyloxy-1-benzyloxymethyl-4-tert-butoxycarbonylamino-2,3-dihydroxy-pentyl)-carbamic acid tert-butyl ester(505085-04-1)

Safety Data

• Hazardous Substances Data: 505085-04-1(Hazardous Substances Data)

Upstream product

• 226931-87-9 1,6-di-O-benzyl-2,5-di-O-methanesulfonyl-3,4-O-methylethylidene-D-mannitol 
• 142285-65-2 3,5-diazido-1,6-di-O-benzyl-2,5-dideoxy-3,4-O-methylethylidene-L-iditol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 505084-92-4 (2S,3R,4R,5S)-2,5-Diazido-1,6-bis-benzyloxy-hexane-3,4-diol 

Downstream Products

• 198417-68-4 (S)-4-Benzyloxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 108149-63-9 tert-butyl (4S)-4-(hydroxymethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 
• 79069-15-1 N-(tert-butyloxycarbonyl)-O-benzyl-L-serinol 

Relevant articles and documents

Regioselective cleavage of the bis-benzylidene acetal of D-mannitol under oxidative and reductive conditions: A new approach to C2-symmetric chiral ligands

A highly regioselective oxidative cleavage of 1,3:4,6-di-O-benzylidene-d- mannitol was carried out using NBS and the resultant product was readily converted to the C2-symmetric chiral ligand, (R,R)-3,4-dihydroxy-1,5- hexadiene. On the other hand, reductive cleavage of 1,3:4,6-di-O-benzylidene-d- mannitol was achieved in a highly regioselective manner using BF 3?OEt2 and Et3SiH to give a highly functionalized benzyl ether, which was converted to a synthetically useful C2-symmetric bis-amino alcohol derivative.

The Lindlar Catalyst Revitalized: A Highly Chemoselective Method for the Direct Conversion of Azides to N-(tert-Butoxycarbonyl)amines

An exceptionally chemoselective method for the direct conversion of azides to N-(tert-butoxycarbonyl)-protected amines under catalytic transfer-hydrogenation conditions, using the Lindlar catalyst, is reported. The extremely labile functional groups such as N-Cbz, benzyl ester are shown to be inert under the reaction conditions. The present method allows us to synthesize orthogonally protected (N-Cbz and N-Boc) 1,2-diamino systems, which will be immensely useful in organic synthesis.