91284-30-9

Basic information

• Product Name: 3-(cyanomethyl)-1-(4-deoxy-6-methyl-alpha-D-lyxo-hexopyranosyluronosyl)-4-methoxy-1H-indole
• CAS NO: 91284-30-9
• Molecular Formula: C₁₈H₂₀N₂O₆
• Molecular Weight: 360.3612
• Mol File: 91284-30-9.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 613.5°C at 760 mmHg
• Flash Point: 324.9°C
• Density: 1.41g/cm³
• Vapor Pressure: 6.57E-16mmHg at 25°C
• Refractive Index: 1.627
• CAS DataBase Reference: 3-(cyanomethyl)-1-(4-deoxy-6-methyl-alpha-D-lyxo-hexopyranosyluronosyl)-4-methoxy-1H-indole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(cyanomethyl)-1-(4-deoxy-6-methyl-alpha-D-lyxo-hexopyranosyluronosyl)-4-methoxy-1H-indole(91284-30-9)
• EPA Substance Registry System: 3-(cyanomethyl)-1-(4-deoxy-6-methyl-alpha-D-lyxo-hexopyranosyluronosyl)-4-methoxy-1H-indole(91284-30-9)

Safety Data

• Hazardous Substances Data: 91284-30-9(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 125287-94-7 methyl 1-(3-cyanomethyl-4-methoxyindol-1-yl)-1,4-dideoxy-2,3-di-O-pivaloyl-α-D-lyxo-hexopyranuronate 
• 160834-15-1 1-O-acetyl-4-deoxy-2,3-di-O-pivaloyl-α-D-lyxohexopyranosyluronic acid methyl ester 
• 73635-99-1 methyl 2,3-O-isopropylidene-4-deoxy-α-D-lyxo-hexopyranoside 
• 125287-90-3 methyl 4-deoxy-2,3-di-O-pivaloyl-α-D-lyxohexopyranosiduronic acid methyl ester 
• 125287-91-4 methyl 1-chloro-1,4-dideoxy-2,3-di-O-pivaloyl-α-D-lyxo-hexopyranuronate 
• 125287-89-0 methyl 2,3-O-isopropylidene-4-deoxy-α-D-lyxohexopyranosiduronic acid methyl ester 
• 160961-46-6 (4S,5S)-dihydroxy-(6S)-methoxytetrahydropyran-(2S)-carboxylic acid methyl ester 

Relevant articles and documents

Synthesis of the Indole Nucleoside Antibiotics Neosidomycin and SF-2140

The indole nucleoside antibiotics neosidomycin 5 and SF-2140 3 have been synthesized.Methyl 4-deoxy-2,3-O-isopropylidene-α-D-lyxo-hexopyranoside 8 was converted into methyl 1-chloro-1,4-dideoxy-2,3-di-O-pivaloyl-α-D-lyxo-hexopyranuronate 33 in five steps.Silver(I)-catalysed coupling of compound 33 with 3-(cyanomethyl)indole 20 gave stereoselectively an α-nucleoside which was converted into methyl 1--1,4-dideoxy-α-D-lyxo-hexopyranuronate (neosidomycin, 5).Coupling of compound 33 to 3-cyanomethyl-4-methoxyindole 23 by the sodium salt procedure, and subsequent deacylation, gave methyl 1-(3-cyanomethyl-4-methoxyindol-1-yl)-1,4-dideoxy-α-D-lyxo-hexopyranuronate (SF-2140, 3).Neosidomycin, SF-2140, and their O-acyl derivatives adopt a conformation which differs from that of 1-(6-O-benzoyl-4-deoxy-2,3-O-pivaloyl-α-D-lyxo-hexopyranosyl)-3-(cyanomethyl)indole 29, in which the methyl uronate grouping of the antibiotics is present at a lower oxidation level.