139631-37-1

Basic information

• Product Name: 3-azido-1,3-dideoxy-1-(phenylsulfenyl)-2,4,6-tri-O-acetyl-β-D-gluco-pyranose
• Synonyms: 3-azido-1,3-dideoxy-1-(phenylsulfenyl)-2,4,6-tri-O-acetyl-β-D-gluco-pyranose
• CAS NO: 139631-37-1
• Molecular Weight: 423.447
• Mol File: 139631-37-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 3-azido-1,3-dideoxy-1-(phenylsulfenyl)-2,4,6-tri-O-acetyl-β-D-gluco-pyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 3-azido-1,3-dideoxy-1-(phenylsulfenyl)-2,4,6-tri-O-acetyl-β-D-gluco-pyranose(139631-37-1)
• EPA Substance Registry System: 3-azido-1,3-dideoxy-1-(phenylsulfenyl)-2,4,6-tri-O-acetyl-β-D-gluco-pyranose(139631-37-1)

Safety Data

• Hazardous Substances Data: 139631-37-1(Hazardous Substances Data)

Upstream product

• 185114-94-7 1,2,4,6-Tetra-O-acetyl-3-azido-3-deoxy-α/β-gluco-hexopyranose 
• 108-98-5 thiophenol 

Downstream Products

• 1417719-98-2 phenyl 3-azido-2,4-di-O-tert-butyldimethylsilyl-3-deoxy-6-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside 
• 1417719-97-1 phenyl 3-azido-3-deoxy-6-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside 
• 12706-94-4 hikizimycin 
• 139631-53-1 3-azido-1,3-dideoxy-1-(phenylsulfenyl)-2,4,6-tri-O-(2,2-dimethylpropanoyl)-β-D-glucopyranose 
• 130861-02-8 3-azido-1,3-dideoxy-1-(phenylsulfinyl)-2,4,6-tri-O-(2,2-dimethylpropanoyl)-β-D-glucopyranose 
• 236115-75-6 4-O-(3-azido-3-deoxy-2,4,6-tri-O-benzyl-α-D-glucopyranosyl)-2-deoxystreptamine 
• 236115-66-5 3-azido-3-deoxy-2,4,6-tri-O-benzyl-1-phenylthio-β-D-glucopyranoside 
• 236401-43-7 4-O-(3-amino-3-deoxy-α-D-glucopyranosyl)-2-deoxystreptamine 
• 688744-61-8 phenyl 3,6-diazido-2,4-di-O-benzyl-3,6-dideoxy-1-thio-β-D-glucopyranoside 
• 729596-96-7 phenyl 3-azido-3-deoxy-6-O-p-tolylsulfonyl-1-thio-β-D-glucopyranoside 
• 868258-59-7 phenyl 4-O-acetyl-3-azido-2,6-di-O-benzyl-3-deoxy-1-thio-β-D-galactopyranoside 
• 868258-58-6 phenyl 3-azido-2,6-di-O-benzyl-3-deoxy-1-thio-β-D-glycopyranoside 

Relevant articles and documents

Synthesis of 3,3′-neotrehalosadiamine and related 1,1′-aminodisaccharides using disarmed, armed, and superarmed building blocks

Here we report a high yielding, stereoselective synthesis of the naturally occurring 1,1′-disaccharide neotrehalosadiamine (NTD) and some related analogs. Following an eleven-step sequence, seven of which did not require chromatographic separation, NTD was generated in 60% overall yield from the inexpensive, commercially available precursor 1,2:5,6-di-O-isopropylidene- α-δ-glucofuranose. The key a,b-linkage of NTD was formed in a highly stereoselective manner by taking advantage of the participating effect of the acyl group at O-2 of the donor glycoside. The influence of electronic effects of disarmed, armed, and superarmed glycosyl donors and acceptors on the outcome of 1,1′-glycosidation was also observed. Antibacterial studies using NTD and its analogs show detectable but weak antistaphylococcal activity.

Total synthesis of (-)-hikizimycin employing the strategy of two-directional chain synthesis

Hikizimycin (anthelmycin) is a nucleoside antibiotic and anthelmintic agent that represents the most structurally complex member of the long-chain carbohydrate class of natural products. The undecose moiety of hikizimycin was constructed efficiently by em