7022-86-8

Basic information

• Product Name: 1,2-O-(1-methylethylidene)-3,5,6-tris-O-[(4-methylphenyl)sulfonyl]hexofuranose
• CAS NO: 7022-86-8
• Molecular Formula: C₃₀H₃₄O₁₂S₃
• Molecular Weight: 682.7788
• Mol File: 7022-86-8.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 801.9°C at 760 mmHg
• Flash Point: 438.8°C
• Density: 1.47g/cm³
• Vapor Pressure: 9.78E-25mmHg at 25°C
• Refractive Index: 1.631
• CAS DataBase Reference: 1,2-O-(1-methylethylidene)-3,5,6-tris-O-[(4-methylphenyl)sulfonyl]hexofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-O-(1-methylethylidene)-3,5,6-tris-O-[(4-methylphenyl)sulfonyl]hexofuranose(7022-86-8)
• EPA Substance Registry System: 1,2-O-(1-methylethylidene)-3,5,6-tris-O-[(4-methylphenyl)sulfonyl]hexofuranose(7022-86-8)

Safety Data

• Hazardous Substances Data: 7022-86-8(Hazardous Substances Data)

Usage

Type of compound

Chemical compound used in organic synthesis and carbohydrate chemistry

Derivative of

Hexofuranose (a six-membered ring sugar molecule)

Function

Protecting group to prevent unwanted reactions at certain hydroxyl groups during chemical reactions

1-methylethylidene group

Present at the 1,2-position

Sulfonyl-protected hydroxyl groups

Three groups present at the 3, 5, and 6-positions

Usefulness

Allows for selective modification and functionalization of carbohydrates

Applications

Synthesis of complex carbohydrates, natural products, and pharmaceutical compounds

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 18549-40-1 1,2-O-isopropylidene-α-D-glucofuranose 
• 582-51-4 1,2-O-isopropylidene-α-D-allofuranose 
• 620630-82-2 1,2 5,6-O-di(isopropylidene)-α-D-allofuranose 

Downstream Products

• 6919-93-3 O²-acetyl-O³,O⁵,O⁶-tris-(toluene-4-sulfonyl)-α-D-glucofuranosyl bromide 
• 88238-34-0 5,6-dideoxy-1,2-O-isopropylidene-3-O-p-tolylsulfonyl-α-D-ribo-hex-5-enofuranose 
• 129709-05-3 C₂₆H₂₉N₃O₁₁S₂ 
• 129709-02-0 C₂₆H₂₉N₃O₁₁S₂ 
• 129709-04-2 C₂₆H₃₁N₃O₁₂S₂ 
• 115319-24-9 C₂₄⁽¹³⁾C₂H₂₉N₃O₁₁S₂ 
• 115319-22-7 C₂₆H₂₉N₃O₁₁S₂ 
• 34885-59-1 C₂₃H₂₈O₁₀S₂ 
• 39022-34-9 3,6-di-O-p-tolylsulfonyl-2,5-anhydro-L-idofuranose dimethylacetal 
• 67492-43-7 6-O-p-tolylsulfonyl-2,5:3,4-dianhydro-L-talofuranose dimethylacetal 
• 115319-27-2 C₂₆H₃₁N₃O₁₂S₂ 
• 115319-26-1 2-Carbamoyl-N-[(R)-2-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-(toluene-4-sulfonyloxy)-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-2-(toluene-4-sulfonyloxy)-ethoxy]-2-imino-acetimidic acid methyl ester 
• 55085-29-5 3,6-di-O-benzoyl-5-deoxy-1,2-O-isopropylidene-α-D-ribo-hexofuranose 
• 88270-97-7 1,2-di-O-acetyl-3,6-di-O-benzoyl-5-deoxy-D-ribo-hexofuranose 

Relevant articles and documents

SYNTHESES OF 1-(5-DEOXY-Β-D-arabino-HEXOFURANOSYL)CYTOSINE

1-(5-Deoxy-β-D-arabino-hexofuranosyl)cytosine (4'-homoara-C) (11), a higher homolog of the antileukemic agent ara-C(1-β-D-arabinofuranosylcytosine), was prepared by two independent routes.The first one involved the inversion of configuration at C-2' of the D-ribo epimer (1-(5-deoxy-β-D-ribo-hexofuranosyl)cytosine, 4'-homocytidine) by the diphenylcarbonate technique; the 5-deoxy-D-ribo-hexofuranosyl moiety of 4'-homocytidine was obtained by way of an anti-Markovnikov addition of iodine trifluoroacetate to the double bond of 5,6-dideoxy-1,2-O-isopropylidene-3-O-p-tolylsulfonyl-α-D-ribo-hex-5-enofuranose and reduction of the resulting iodide(s).In the second approach, 5-deoxy-1,2-O-isopropylidene-3-O-p-tolylsulfonyl-β-D-xylo-hexofuranose was acetolyzed and condensed with 4-acetyl-N-bis(trimethylsilyl)cytosine, and alkaline treatment gave 11 by way of a 2',3'-anhydro intermediate.The structure of 11, in particular the configuration at C-2', was confirmed by its 1H- and 13C-n.m.r. spectra.