142285-65-2

Basic information

• Product Name: 3,5-diazido-1,6-di-O-benzyl-2,5-dideoxy-3,4-O-methylethylidene-L-iditol
• Synonyms: 3,5-diazido-1,6-di-O-benzyl-2,5-dideoxy-3,4-O-methylethylidene-L-iditol
• CAS NO: 142285-65-2
• Molecular Weight: 452.513
• Mol File: 142285-65-2.mol

Chemical Properties

• CAS DataBase Reference: 3,5-diazido-1,6-di-O-benzyl-2,5-dideoxy-3,4-O-methylethylidene-L-iditol(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-diazido-1,6-di-O-benzyl-2,5-dideoxy-3,4-O-methylethylidene-L-iditol(142285-65-2)
• EPA Substance Registry System: 3,5-diazido-1,6-di-O-benzyl-2,5-dideoxy-3,4-O-methylethylidene-L-iditol(142285-65-2)

Safety Data

• Hazardous Substances Data: 142285-65-2(Hazardous Substances Data)

Upstream product

• 100-51-6 benzyl alcohol 
• 63700-05-0 1,2;5,6-dianhydro-3,4-O-isopropylidene-D-mannitol 
• 3969-84-4 3,4-di-O-isopropylidene-D-mannitol 
• 142285-64-1 1,6-di-O-benzyl-3,4-O-methylethylidene-D-mannitol 
• 100-39-0 benzyl bromide 
• 77-76-9 2,2-dimethoxy-propane 
• 257881-05-3 Methanesulfonic acid (1R,2S,3S,4R)-5-benzyloxy-1-benzyloxymethyl-2,3-dihydroxy-4-methanesulfonyloxy-pentyl ester 
• 151061-71-1 2,5-Di-O-mesyl-1,3:4,6-di-O-benzylidene-D-mannitol 
• 100-52-7 benzaldehyde 
• 69-65-8 mannitol 
• 61490-28-6 1,3:4,6-di-O-benzylidene-D-mannitol 
• 226931-87-9 1,6-di-O-benzyl-2,5-di-O-methanesulfonyl-3,4-O-methylethylidene-D-mannitol 

Downstream Products

• 142285-66-3 3,5-diamino-1,6-di-O-benzyl-2,5-dideoxy-3,4-O-methylethylidene-L-iditol 
• 505084-92-4 (2S,3R,4R,5S)-2,5-Diazido-1,6-bis-benzyloxy-hexane-3,4-diol 
• 267895-50-1 (4S,5R,6R,7S)-4,7-dibenzyloxymethyl-5,6-dihydroxy-5,6-O-methylethylidene-2-(N-benzyl)-imino-1,3-diazepane 
• 267895-47-6 (4S,5R,6R,7S)-4,7-dibenzyloxymethyl-5,6-dihydroxy-5,6-O-methylethylidene-1,3-diazepan-2-thione 
• 505085-04-1 (5-benzyloxy-1-benzyloxymethyl-4-tert-butoxycarbonylamino-2,3-dihydroxy-pentyl)-carbamic acid tert-butyl ester 
• 198417-68-4 (S)-4-Benzyloxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 79069-15-1 N-(tert-butyloxycarbonyl)-O-benzyl-L-serinol 
• 79069-54-8 (S)-2-(t-butoxycarbonylamino)-3-phenylmetoxy-1-propanal 
• 109075-06-1 (S)-2-((4R,5R)-2,2-dimethyl-5-((S)-1-tosylaziridin-2-yl)-1,3-dioxolan-4-yl)-1-tosyl-aziridine 
• 914982-47-1 (2R,3S,4S,5R)-1,6-bis(benzyloxy)-3,4-bis((methylsulfonyl)oxy)-N₂,N₅-ditosylhexane-2,5-diamine 
• 914982-45-9 (S)-2-benzyloxy-1-((4R,5R)-5-((S)-2-benzyloxy-1-(tosylamino)ethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-N-tosylethanamine 
• 914982-46-0 (2S,3R,4R,5S)-1,6-bis(benzyloxy)-2,5-bis(tosylamino)hexane-3,4-diol 
• 914982-48-2 (2R,3R)-2-((benzyloxy)methyl)-3-((2R,3R)-3-((benzyloxy)methyl)-1-tosylaziridin-2-yl)-1-tosylaziridine 
• 914982-51-7 Methanesulfonic acid (S)-2-{(4R,5R)-5-[(S)-2-methanesulfonyloxy-1-(toluene-4-sulfonylamino)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-(toluene-4-sulfonylamino)-ethyl ester 

Relevant articles and documents

Synthesis of enantiopure bis-aziridines, bis-epoxides, and aziridino-epoxides from d-mannitol

A practical synthesis of enantiopure bis-aziridines 11 and 15, bis-epoxides 12 and 17, and aziridino-epoxides 27 and 30 is reported using inexpensive d-mannitol as the starting material. The key transformation involves the reductive cleavage of bis-benzyl

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.

Synthesis of C2-symmetric guanidino-sugars as potent inhibitors of glycosidases

A series of enantiomerically pure C2-Symmetric guanidino-sugars was synthesized from D-mannitol. The first method described involves direct opening of a bis-epoxide by guanidine, whereas the second one deals with a mercury-catalyzed transformation of a cyclic thiourea into a N,N',N'- trisubstituted guanidine as a key step. The biological activity of these compounds towards several glycosidases has been evaluated. One of them (5) was found to selectively inhibit α-L-fucosidase of bovin kidney (2.8 μM). (C) 2000 Elsevier Science Ltd.

Synthesis of C2-symmetrical cyclic guanidino-sugars from D-mannitol

An efficient method for the synthesis of C2-symmetrical cyclic guanidino-sugars has been developed from 1,2:5,6-dianhydro-3,4-O-methylethylidene-D-mannitol or L-iditol.