20221-50-5

Basic information

• Product Name: 1,2,5,6-hexanetetrol
• CAS NO: 20221-50-5
• Molecular Weight: 150.175
• Mol File: 20221-50-5.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: 1,2,5,6-hexanetetrol(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,5,6-hexanetetrol(20221-50-5)
• EPA Substance Registry System: 1,2,5,6-hexanetetrol(20221-50-5)

Safety Data

• Hazardous Substances Data: 20221-50-5(Hazardous Substances Data)

Upstream product

• 592-42-7 1,5-Hexadien 
• 6973-62-2 2,5-Bis-acetoxymethyl-tetrahydro-furan 
• 64-17-5 ethanol 
• 57-50-1 Sucrose 
• 50-70-4 D-sorbitol 
• 69-65-8 mannitol 
• 3427-24-5 (2S,3E,5S)-1,2,5,6-tetrahydroxy-1,2:5,6-di-O-isopropylidene-hex-3-ene 
• 56-81-5 glycerol 
• 37112-31-5 levoglucosenone 
• 97-30-3 methyl D-glucopyranoside 
• 67-47-0 5-hydroxymethyl-2-furfuraldehyde 
• 3615-56-3 D-Sorbose 
• 98-59-9 p-toluenesulfonyl chloride 
• 104-80-3 tetrahydrofuran-2,5-dimethanol 

Downstream Products

• 74892-52-7 C₂₀H₂₆O₈S₂ 
• 104-80-3 tetrahydrofuran-2,5-dimethanol 
• 2889-31-8 2-hydroxyglutaric acid 
• 13544-77-9 2,5-dihydroxyadipic acid 
• 204120-35-4 (2R,5R)-1-Benzyl-2,5-bis-methoxymethoxymethyl-pyrrolidine 
• 204120-25-2 C₃₂H₅₄O₈S₂Si₂ 
• 157008-40-7 trans-N-benzyl-2,5-bis(hydroxymethyl)pyrrolidine 
• 93713-36-1 1-Benzyl-[(2R,5R)-2,5-bis(hydroxymethyl)]pyrrolidine 

Relevant articles and documents

CATALYTIC PRODUCTION OF 1,2,5,6-HEXANETETROL FROM LEVOGLUCOSENONE

A method of making of 1,2,5,6-hexanetetrol ("tetrol"). The method includes the steps of contacting a reaction solution containing water as well as levoglucosenone, dihydrolevoglucosenone, and/or levoglucosanol, with a catalyst ontaining metal and acid functionalities, at temperature of from about 100 °C to about 175 °C, and a hydrogen partial pressure of from about 1 bar to about 50 bar (about 0.1 MPa to about 5 MPa), and for a time wherein at least a portion of the reactant is converted into 1,2,5,6-hexanetetrol.

SYNTHESIS OF R-GLUCOSIDES, SUGAR ALCOHOLS, REDUCED SUGAR ALCOHOLS, AND FURAN DERIVATIVES OF REDUCED SUGAR ALCOHOLS

Disclosed herein are methods for synthesizing 1,2,5,6-hexanetetrol (HTO), 1,6 hexanediol (HDO) and other reduced polyols from C5 and C6 sugar alcohols or R glycosides. The methods include contacting the sugar alcohol or R-glycoside with a copper catalyst, most desirably a Raney copper catalyst with hydrogen for a time, temperature and pressure sufficient to form reduced polyols having 2 to 3 fewer hydoxy groups than the starting material. When the starting compound is a C6 sugar alcohol such as sorbitol or R-glycoside of a C6 sugar such as methyl glucoside, the predominant product is HTO. The same catalyst can be used to further reduce the HTO to HDO.

Symmetry-Assisted Synthesis of C2-Symmetric trans-α,α'-Bis(hydroxymethyl)pyrrolidine and -piperidine Derivatives via Double Sharpless Asymmetric Dihydroxylation of αω-Terminal Dienes

A new strategy has been developed for the synthesis of C2-symmetric trans-α,α'-bis(hydroxymethyl)pyrrolidine and piperidine derivatives 1-3 starting from symmetric αω-terminal dienes 4-6. The double-asymmetric dihydroxylation (AD) reaction of 4-6 gave C2-symmetric tetrols, which were converted in a four-step sequence to C2-symmetric azacycloalkanes 17,9, and 22, respectively. These azacycloalkanes were transformed into 1-3 in high enantiomeric excess (82% → 98%ee). The double AD reaction proved to cause enantiomeric enhancement, even though the asymmetric induction for the first AD reaction is moderate. In addition, it was observed that the chromatography on silica gel of several C2-symmetric azacycloalkanes (17, 20, and 22) of varying ee's resulted in marked enantiomeric fractionation.