194991-50-9

Basic information

• Product Name: (2S,3S,4R,5S)-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
• Synonyms: (2S,3S,4R,5S)-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
• CAS NO: 194991-50-9
• Molecular Weight: 164.158
• Mol File: 194991-50-9.mol

Chemical Properties

• CAS DataBase Reference: (2S,3S,4R,5S)-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S,4R,5S)-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol(194991-50-9)
• EPA Substance Registry System: (2S,3S,4R,5S)-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol(194991-50-9)

Safety Data

• Hazardous Substances Data: 194991-50-9(Hazardous Substances Data)

Upstream product

• 20197-42-6 tagatose (β-pyranose) 
• 137396-21-5 1,2,3,4-Tetra-O-acetyl-5,6-didesoxy-6-phenylsulfinyl-D-xylohexitol 
• 137396-20-4 1,2,3,4-Tetra-O-acetyl-5-desoxy-6-S-phenyl-6-thio-D-xylo-hexitol 
• 137396-19-1 5-Desoxy-6-S-phenyl-6-thiofructose 
• 137396-22-6 1,3,4,5,6-Penta-O-acetyl-2-desoxy-L-gulo-S-phenyl-hemithioacetal 

Relevant articles and documents

Selective C?O Bond Cleavage of Sugars with Hydrosilanes Catalyzed by Piers’ Borane Generated In Situ

Described herein is the selective reduction of sugars with hydrosilanes catalyzed by using Piers’ borane [(C6F5)2BH] generated in situ. The hydrosilylative C?O bond cleavage of silyl-protected mono- and disaccharides in the presence of a (C6F5)2BH catalyst, generated in situ from (C6F5)2BOH, takes place with excellent chemo- and regioselectivities to provide a range of polyols. A study of the substituent effects of sugars on the catalytic activity and selectivity revealed that the steric environment around the anomeric carbon (C1) is crucial.

Chemo-Enzymatic Synthesis of Carbohydrates: The Preparation of L-Xylose and 2-Deoxy-L-xylo-hexose

A synthetic approach to L-xylose (6) and 2-deoxy-L-xylo-hexose (8) has been developed.The strategy utilizes achiral starting materials and employs two enzymatic reactions to introduce the desired chiral centers.Rabbit muscle aldolase (RAMA)-catalyzed condensation of (3-phenylthio)propanal (1) with dihydroxyacetone phosphate (DHAP) affords the C-6 skeleton 2 with D-threo configuration between C-3 and C-4.Diastereoselective reduction of 2 with sorbitol dehydrogenase (SDH) introduces the final stereocenter of the tetrahydroxy derivative 3.After oxidation of sulfide 3 to the corresponding diastereotopic sulfoxides 4, L-xylose (6) is obtained by thermal elimination of phenylsulfenic acid followed by ozonolysis. 2-Deoxy-L-xylo-hexose (8) is yielded from 4 by a Pummerer rearrangement and subsequent reductive deprotection (DIBAL-H) of the rearrangement product 7. Key Words: L-Xylose / 2-Deoxy-L-xylo-hexose / Enzymatic syntheses / Carbohydrates