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

Description

alpha-l-Sorbofuranose, 2,3-O-(1-methylethylidene)-, also known as 2,3-O-Isopropylidene-α-L-sorbofuranose (CAS# 17682-71-2), is a white to off-white solid compound with significant utility in the field of organic synthesis. Its unique chemical structure allows for various applications across different industries.

Uses

Used in Organic Synthesis:
alpha-l-Sorbofuranose, 2,3-O-(1-methylethylidene)is used as a key compound in organic synthesis for its ability to facilitate the creation of complex organic molecules. Its unique structure makes it a valuable building block for the development of new pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, alpha-l-Sorbofuranose, 2,3-O-(1-methylethylidene)is used as an intermediate in the synthesis of various drugs. Its versatility in organic synthesis allows for the development of novel drug candidates with potential therapeutic applications.
Used in Agrochemical Industry:
alpha-l-Sorbofuranose, 2,3-O-(1-methylethylidene)is also utilized in the agrochemical industry for the synthesis of new pesticides and other crop protection agents. Its unique properties enable the development of more effective and environmentally friendly products.
Used in Specialty Chemicals Industry:
In the specialty chemicals industry, alpha-l-Sorbofuranose, 2,3-O-(1-methylethylidene)is used as a starting material for the synthesis of various specialty chemicals, such as fragrances, dyes, and additives. Its unique chemical structure contributes to the development of innovative products with specific applications in various markets.

Upstream product

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

Downstream Products

• 126210-25-1 6-azido-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 
• 126210-26-2 6-(benzyloxycarbonyl)amino-6-desoxy-2,3-O-isopropylidene-α-L-sorbofuranose 
• 19130-96-2 1,5-dideoxy-1,5-imino-D-glucitol 
• 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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