17682-71-2

Basic information

• Product Name: alpha-l-Sorbofuranose, 2,3-O-(1-methylethylidene)-
• Synonyms: alpha-l-Sorbofuranose, 2,3-O-(1-methylethylidene)-;2,3-O-Isopropylidene-α-L-sorbofuranose;1-O,2-O-Isopropylidene-1-(hydroxymethyl)-α-L-xylofuranose;2-O,3-O-(1-Methylethylidene)-α-L-sorbofuranose;2,3-O-(1-Methylethylidene)-α-L-sorbofuranose
• CAS NO: 17682-71-2
• Molecular Formula: C₉H₁₆O₆
• Molecular Weight: 220.21974
• EINECS: 241-664-3
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives
• Mol File: 17682-71-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: 93-95°C
• Boiling Point: 393.7°Cat760mmHg
• Flash Point: 191.9°C
• Appearance: /
• Density: 1.347g/cm³
• Storage Temp.: -20°C Freezer
• Solubility: Methanol (Slightly), Water (Slightly)
• CAS DataBase Reference: alpha-l-Sorbofuranose, 2,3-O-(1-methylethylidene)-(CAS DataBase Reference)
• NIST Chemistry Reference: alpha-l-Sorbofuranose, 2,3-O-(1-methylethylidene)-(17682-71-2)
• EPA Substance Registry System: alpha-l-Sorbofuranose, 2,3-O-(1-methylethylidene)-(17682-71-2)

Safety Data

• Hazardous Substances Data: 17682-71-2(Hazardous Substances Data)

Usage

Chemical Properties

White to Off-White Solid

Uses

2,3-O-Isopropylidene-α-L-sorbofuranose (cas# 17682-71-2) is a compound useful in organic synthesis.

Upstream product

• 470-15-5 α-L-sorbopyranose 
• 67-64-1 acetone 
• 87-79-6 L-sorbose 
• 7664-93-9 sulfuric acid 
• 20977-14-4 1-O-acetyl-2,3:4,6-di-O-isopropylidene-α-L-sorbofuranose 
• 17682-70-1 2,3:4,6-bis-O-isopropylidene-L-sorbose 
• 7270-77-1 L-sorbopyranose 
• 35673-97-3 L-sorbose 

Downstream Products

• 126210-25-1 6-azido-6-desoxy-2,3-O-isopropylidene-α-L-sorbofuranose 
• 19130-96-2 1,5-dideoxy-1,5-imino-D-glucitol 
• 126210-26-2 6-(benzyloxycarbonyl)amino-6-desoxy-2,3-O-isopropylidene-α-L-sorbofuranose 
• 83032-12-6 O²,O³-isopropylidene-6-iodo-O¹-(toluene-4-sulfonyl)-6-deoxy-α-L-sorbofuranose 
• 82064-03-7 O²,O³-isopropylidene-O¹-(toluene-4-sulfonyl)-6-deoxy-α-L-sorbofuranose 
• 96480-54-5 fructose-1,6-bisphosphate 
• 73861-92-4 1,5,6-trideoxy-1,5-imino-D-glucitol 
• 1121-25-1 2-methyl-3-pyridinol 
• 210174-73-5 1,5,6-trideoxy-1,5-imino-D-glucitol hydrochloride 
• 910222-11-6 6-azido-6-deoxy-2,3-O-isopropylidene-1-O-(p-toluenesulfonyl)-α-L-sorbofuranose 
• 910222-14-9 N-benzyloxycarbonyl-1,5,6-trideoxy-1,5-imino-D-glucitol 
• 266306-66-5 6-O-(tert-Butyldiphenylsilyl)-2,3-O-isopropylidene-α-L-sorbofuranose 
• 2484-55-1 2,3-O-isopropylidene-1,6-bis-O-(p-toluenesulfonyl)-α-L-sorbofuranose 

Relevant articles and documents

A reinvestigation of the synthesis and revision of spectral data of 1,2-O-isopropylidene-α-l-sorbofuranose, 1,2:4,6-di-O-isopropylidene- α-l-sorbofuranose and derivatives

Mono- and di-O-isopropylidene-l-sorbofuranose derivatives are important starting materials for the synthesis of modified sugars and useful chiral compounds. However, several inconsistencies in the spectral data of these compounds and erroneous structural assignments have been noted in the literature. The unambiguous synthesis of 1,2:4,6-di-O-isopropylidene-α-l- sorbofuranose and derivatives of 1,2- and 2,3-O-isopropylidene-α-l- sorbofuranoses has been achieved and definitive spectral data on these compounds are provided.

α-Chloronitroso compounds derived from carbohydrate ketones: Cycloadditions with cyclic dienes, a synthesis of (-)-physoperuvine and a formal synthesis of (+)-epibatidine

1,2-O-Isopropylidene-α-D-xylofuranose 9 was converted into 5-O-(tert-butyldiphenylsilyl)-3-chloro-3-deoxy-1,2-O-isopropylidene-3-C-nitroso- α-o-xylofuranose 17 in four steps, and a similar α-chloronitroso compound 8 was synthesised from 1,2:5,6-di-O-isopropylidene-α-o-glucofuranose 6, the structures of 8 and 17 being confirmed by X-ray crystallography. Reaction of 8 or 17 with cyclohexa-1,3-diene in the presence of small amounts of water gave the cycloadduct (1S,4R)-3-aza-2-oxabicyclo[2.2.2]oct-5-ene, as its hydrochloride (-)-2, in ≥96% ee. Reactions of either 8 or 17 with cyclohepta-1,3-diene similarly gave (1R,5S)-7-aza-6-oxabicyclo[3.2.2]non-8-ene hydrochloride (-)-25 with ≥96% ee, but reactions with cyclopentadiene proceeded differently, with 17 giving the nitrone (E)-(3 R,5 R)-3-[5′-O-(tert-butyldiphenylsilyl)-3′-deoxy-1′,2′-O-is opropylidene-α-D-erythro-pentofuranos-3′-ylidene-amino]-5-chlorocycl opentene N-oxide 19, the structure of which was determined by X-ray crystallography. The dihydrooxazines (-)-25 and (-)-2 were used in syntheses of (-)-physoperuvine (-)-34 and (+)-epibatidine (+)-40, respectively. A pseudoenantiomeric α-chloronitroso compound 51 was also prepared from 2,3-O-isopropylidene-α-L-sorbofuranose 44, and reaction of 51 with cyclohexa-1,3-diene gave (+)-2 with 97% ee.

CHEMICAL REACTION MECHANISM IN ACETONATION OF L-SORBOSE

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