Methyl 2,3,6-trideoxy-alpha-glycero-hex-2-enopyranosid-4-ulose

Base Information

• Chemical Name: Methyl 2,3,6-trideoxy-alpha-glycero-hex-2-enopyranosid-4-ulose
• CAS No.: 33647-82-4
• Molecular Formula: C₇H₁₀O₃
• Molecular Weight: 142.155
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID00187325
• Wikidata: Q83058982
• Mol file: 33647-82-4.mol

Synonyms:methyl 2,3,6-trideoxy-alpha-glycero-hex-2-enopyranosid-4-ulose;MTHPU

Chemical Property of Methyl 2,3,6-trideoxy-alpha-glycero-hex-2-enopyranosid-4-ulose

Chemical Property:

• Vapor Pressure: 0.0447mmHg at 25°C
• Boiling Point: 237.5°Cat760mmHg
• Flash Point: 87.9°C
• PSA: 35.53000
• Density: 1.09g/cm³
• LogP: 0.50290
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 142.062994177
• Heavy Atom Count: 10
• Complexity: 162

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(=O)C=CC(O1)OC
• Isomeric SMILES: C[C@@H]1C(=O)C=C[C@H](O1)OC

Technology Process of Methyl 2,3,6-trideoxy-alpha-glycero-hex-2-enopyranosid-4-ulose

There total 9 articles about Methyl 2,3,6-trideoxy-alpha-glycero-hex-2-enopyranosid-4-ulose 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: 85.0%

Methyl-2,3-anhydro-6-desoxy-α-D-ribo-hexopyranosid-4-ulose (55533-59-0,55533-65-8,59463-87-5,60269-19-4) → methyl 2,3,6-trideoxy-α-D-glycero-hex-2-enopyranosid-4-ulose (33647-82-4)

Guidance literature:

With N-methyl-1,3-benzothiazole-2(3H)-selone; trifluoroessigsaeure; In dichloromethane; at 25 ℃; for 5h;

DOI:10.1055/s-1980-29149

Reference yield: 82.0%

methanol (67-56-1) + carbonic acid tert-butyl ester 5-methyl-5,6-dihydro-2H-pyran-2-yl ester → methyl 2,3,6-trideoxy-α-D-glycero-hex-2-enopyranosid-4-ulose (33647-82-4)

Guidance literature:

With triphenylphosphine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex;

DOI:10.1021/jo800691v

Reference yield: 21.0%

1-(2,5-dimethoxy-2,5-dihydrofuran-2-yl)ethanol from 2-Acetylfuran (33647-67-5,316186-17-1,236408-20-1) → methyl 2,3,6-trideoxy-α-DL-glycero-hex-2-enopyranosid-4-ulose (33647-82-4,33647-83-5,41728-10-3,55102-46-0,55102-47-1,71049-76-8,71049-77-9,97372-42-4,116502-24-0) + methyl 2,3,6-trideoxy-β-DL-glycero-hex-2-enopyranosid-4-ulose (33647-82-4,33647-83-5,41728-10-3,55102-46-0,55102-47-1,71049-76-8,71049-77-9,97372-42-4,116502-24-0)

Guidance literature:

With formic acid; In methanol; for 0.0833333h; Ambient temperature;

upstream raw materials:

Methyl-2,3-anhydro-6-desoxy-α-D-ribo-hexopyranosid-4-ulose

1-(2,5-dimethoxy-2,5-dihydrofuran-2-yl)ethanol from 2-Acetylfuran

1-(2-furyl)ethanol

1-(2-furyl)-1-ethanone

Downstream raw materials:

methyl 3-benzamido-2,3,6-trideoxy-α-DL-lyxo-hexopyranoside

(+/-)-Ristosamine methyl ether

methyl 3-benzamido-4-O-benzoyl-2,3,6-trideoxy-α-DL-lyxo-hexopyranoside

methyl 4-O-(N-benzoylbenzimidoyl)-2,3,6-trideoxy-α-DL-threo-hex-2-enopyranoside