(3S,4R,5S)-3,4,5,6-tetrahydroxyhexanal

Base Information

• Chemical Name: (3S,4R,5S)-3,4,5,6-tetrahydroxyhexanal
• CAS No.: 25029-33-8
• Deprecated CAS: 2092-72-0,3724-71-8,4825-30-3,7640-18-8
• Molecular Formula: C₆H₁₂O₅
• Molecular Weight: 164.158
• Hs Code.: 2912491000
• European Community (EC) Number: 205-823-0,217-765-3
• DSSTox Substance ID: DTXSID80590813
• Metabolomics Workbench ID: 49900
• NCI Thesaurus Code: C116618
• Nikkaji Number: J495.983C
• Wikipedia: 2-Deoxy-D-glucose
• Mol file: 25029-33-8.mol

Synonyms:2 Deoxy D glucose;2 Deoxyglucose;2 Desoxy D glucose;2-Deoxy-D-glucose;2-Deoxyglucose;2-Desoxy-D-glucose;Deoxyglucose

Chemical Property of (3S,4R,5S)-3,4,5,6-tetrahydroxyhexanal

Chemical Property:

• Boiling Point: 456.7 °C at 760 mmHg
• PKA: 13.47±0.20(Predicted)
• Flash Point: 244.1 °C
• PSA: 97.99000
• Density: 1.414 g/cm³
• LogP: -2.34960
• XLogP3: -2.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 164.06847348
• Heavy Atom Count: 11
• Complexity: 116

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C=O)C(C(C(CO)O)O)O
• Isomeric SMILES: C(C=O)[C@@H]([C@H]([C@H](CO)O)O)O
• Recent ClinicalTrials: A Controlled Human Rhinovirus Infection Study of 2-Deoxy-D-Glucose in Healthy Adults

Technology Process of (3S,4R,5S)-3,4,5,6-tetrahydroxyhexanal

There total 9 articles about (3S,4R,5S)-3,4,5,6-tetrahydroxyhexanal which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

Acetic acid (2S,3R)-3-(R)-4,5-dihydro-isoxazol-5-yl-2,3-dihydroxy-propyl ester (104048-45-5,104111-63-9) → 2-deoxy-xylo-hexose (154-17-6,1949-89-9,6605-21-6,6664-99-9,7087-86-7,19479-13-1,23583-41-7,25029-33-8,52248-62-1,64625-39-4,85115-07-7,104111-65-1,104111-68-4,143168-79-0)

Guidance literature:

With hydrogen; Pd-BaSO₄; In methanol; water; for 2h;

DOI:10.1016/S0040-4020(01)91358-4

Reference yield:

(E)-2,4-pentadien-1-ol (4949-20-6,52192-01-5) → 2-deoxy-xylo-hexose (154-17-6,1949-89-9,6605-21-6,6664-99-9,7087-86-7,19479-13-1,23583-41-7,25029-33-8,52248-62-1,64625-39-4,85115-07-7,104111-65-1,104111-68-4,143168-79-0)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine; CCl₄ / 0 °C

2: N-chlorosuccinimide, Me₃SiCl, Et₃N, CF₃COOH / CHCl₃

3: OsO₄, H₂O₂ / acetone; H₂O / 0 °C

4: H₂ / Pd/BaSO₄ / methanol; H₂O / 2 h

With N-chloro-succinimide; osmium(VIII) oxide; chloro-trimethyl-silane; hydrogen; dihydrogen peroxide; triethylamine; trifluoroacetic acid; Pd-BaSO₄; In pyridine; methanol; tetrachloromethane; chloroform; water; acetone;

DOI:10.1016/S0040-4020(01)91358-4

Reference yield:

trans-2,4-pentadienyl acetate (63780-11-0) → 2-deoxy-xylo-hexose (154-17-6,1949-89-9,6605-21-6,6664-99-9,7087-86-7,19479-13-1,23583-41-7,25029-33-8,52248-62-1,64625-39-4,85115-07-7,104111-65-1,104111-68-4,143168-79-0)

Guidance literature:

Multi-step reaction with 3 steps

1: N-chlorosuccinimide, Me₃SiCl, Et₃N, CF₃COOH / CHCl₃

2: OsO₄, H₂O₂ / acetone; H₂O / 0 °C

3: H₂ / Pd/BaSO₄ / methanol; H₂O / 2 h

With N-chloro-succinimide; osmium(VIII) oxide; chloro-trimethyl-silane; hydrogen; dihydrogen peroxide; triethylamine; trifluoroacetic acid; Pd-BaSO₄; In methanol; chloroform; water; acetone;

DOI:10.1016/S0040-4020(01)91358-4

upstream raw materials:

Acetic acid (2S,3R)-3-(R)-4,5-dihydro-isoxazol-5-yl-2,3-dihydroxy-propyl ester

(E)-2,4-pentadien-1-ol

trans-2,4-pentadienyl acetate

Acetic acid (E)-3-(4,5-dihydro-isoxazol-5-yl)-allyl ester