29747-91-9

Basic information

• Product Name: 1,2-O-ISOPROPYLIDENE-BETA-L-IDOFURANOSE
• Synonyms: 1,2-O-ISOPROPYLIDENE-BETA-L-IDOFURANOSE;1,2-O-ISOPROPYLIDENE-SS-L-IDOFURANOSE;1,2-O-Isopropylidene-β-L-idofuranose
• CAS NO: 29747-91-9
• Molecular Formula: C₉H₁₆O₆
• Molecular Weight: 220.21974
• Mol File: 29747-91-9.mol
• Article Data: 7

Chemical Properties

• Melting Point: 113-115 °C
• Appearance: /
• Storage Temp.: −20°C
• CAS DataBase Reference: 1,2-O-ISOPROPYLIDENE-BETA-L-IDOFURANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-O-ISOPROPYLIDENE-BETA-L-IDOFURANOSE(29747-91-9)
• EPA Substance Registry System: 1,2-O-ISOPROPYLIDENE-BETA-L-IDOFURANOSE(29747-91-9)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 29747-91-9(Hazardous Substances Data)

Usage

Class

Furanoses

Derivative

L-idose, a rare sugar and important intermediate in the synthesis of various bioactive compounds

Use

Protecting group for the hydroxyl group of sugar to prevent unwanted reactions during chemical synthesis

Applications

Synthesis of complex carbohydrates and glycosides, development of pharmaceuticals and agrochemicals

Molecular weight

190.19 g/mol

Synthesis

Typically obtained through chemical synthesis

Upstream product

• 7284-07-3 5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-eno-furanose 
• 620630-82-2 1,2 5,6-O-di(isopropylidene)-α-D-allofuranose 
• 329899-64-1 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 38166-60-8 1,2:5,6-di-O-isopropylidene-α-L-glucofuranoside 
• 4118-60-9 5,6-anhydro-1,2-O-isopropylidene-β-L-idofuranose 
• 19684-32-3 1,2-O-isopropylidene-α-D-xylo-hexafuranos-5-ulose 
• 1990-29-0 D-altrose 
• 67-64-1 acetone 

Downstream Products

• 848345-27-7 6-O-t-butyldiphenylsilyl-1,2-O-isopropylidene-β-L-idofuranose 
• 848345-34-6 (1S,4S,5R,6S,7R)-6,7-dibenzyloxy-5-nitro-2-oxabicyclo-[2.2.1]heptan-3-one 
• 848345-33-5 3,5-di-O-benzyl-6-deoxy-6-nitro-β-L-idono-1,4-lactone 
• 848345-36-8 methyl 3,5-di-O-benzyl-6-deoxy-6-nitro-L-idofuranoside 
• 848345-31-3 3,5-di-O-benzyl-6-deoxy-6-iodo-1,2-O-isopropylidene-β-L-idofuranose 
• 848345-29-9 3,5-di-O-benzyl-1,2-O-isopropylidene-β-L-idofuranose 
• 848345-32-4 3,5-di-O-benzyl-6-deoxy-6-nitro-1,2-O-isopropylidene-β-L-idofuranose 
• 848345-30-2 3,5-di-O-benzyl-6-O-p-toluenesulfonyl-1,2-O-isopropylidene-β-L-idofuranose 
• 848345-28-8 3,5-di-O-benzyl-6-O-t-butyldiphenylsilyl-1,2-O-isopropylidene-β-L-idofuranose 
• 1392131-82-6 N-benzyl-6-O-tert-butyldimethylsilyl-3,5-dideoxy-3,5-imino-1,2-O-isopropylidene-alpha-D-gulofuranose 
• 1392131-83-7 N-benzyl-2,4-dideoxy-2,4-imino-D-glucitol 
• 1392131-84-8 (2E)-methyl-(4R,5R,6R,7S)-N-benzyl-4,6,8-trihydroxy-5,7-iminooct-2-enoate 
• 1392131-86-0 (2E)-methyl-(4R,5R,6R,7S)-N-benzyl-4,6,8-tris(tert-butyldimethylsilyloxy)-5,7-iminooct-2-enoate 
• 180336-16-7 1,2-O-isopropylidene-3,5,6-tri-O-benzyl-α-D-glucofuranose 

Relevant articles and documents

Synthesis from d-altrose of (5 R,6 R,7 R,8 S)-5,7-dihydroxy-8- hydroxymethylconidine and 2,4-dideoxy-2,4-imino-d-glucitol, azetidine analogues of swainsonine and 1,4-dideoxy-1,4-imino-d-mannitol

Ring closure of a 3,5-di-O-triflate derived from d-altrose with benzylamine allowed the formation of both monocyclic and bicyclic azetidine analogues of swainsonine.

The role of the C-3 substituent in the asymmetric dihydroxylation of hexo-5-enofuranosides

Asymmetric dihydroxylation of vinyl furanosides 1-6 by use of OsO4, AD-mix-α and β is described yielding the corresponding hexofuranose sugars. Vinyl furanosides 2 and 3, with an ester group at C-3, and vinyl manno furanoside 5 on asymmetric dihydroxylation with AD-mix α exhibited high R diastereoselectivity at C-5. Reversal in diastereoselectivity at C-5 was observed for the 3-deoxy vinyl furanoside 6 giving furanosaccharide 6S with the S configuration at C-5.

PRACTICAL SYNTHESIS OF NOJIRIMYCIN

The short step and efficient synthesis of nojirimycin (1) from commercially available 1,2-isopropylidene-D-glucofuranose (2) was described.Oxidation of 2 with (Bu3Sn)2O-Br2 followed by oximation, isomerization, and stereoselective reduction gave the 5-amino derivative of gluco-configuration (6a), which was converted to nojirimycin bisulfite adduct (8) in 50percent overall isolated yield.