3,4-Dihydroxy-5-(hydroxymethyl)-3-methyloxolan-2-one

Base Information

• Chemical Name: 3,4-Dihydroxy-5-(hydroxymethyl)-3-methyloxolan-2-one
• CAS No.: 492-30-8
• Molecular Formula: C₆H₁₀O₅
• Molecular Weight: 162.142
• Hs Code.: 2932190090
• NSC Number: 244799,62382,19768
• Mol file: 492-30-8.mol

Synonyms:NSC19768;SCHEMBL3300535;BCP11226;NSC62382;NSC-19768;NSC-62382;NSC244799;NSC-244799;SY225343;FT-0660777;53008-96-1

Chemical Property of 3,4-Dihydroxy-5-(hydroxymethyl)-3-methyloxolan-2-one

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 150-160oC
• Boiling Point: 338.3 °C at 760 mmHg
• PKA: 12.12±0.60(Predicted)
• Flash Point: 145.6 °C
• PSA: 86.99000
• Density: 1.512 g/cm³
• LogP: -1.98400
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 162.05282342
• Heavy Atom Count: 11
• Complexity: 180

Purity/Quality:

99% ^*data from raw suppliers

2-C-Methyl-D-ribono-1,4-lactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(C(OC1=O)CO)O)O
• Uses: 2-C-Methyl-D-ribono-1,4-lactone is used in synthesis of enantiomerically pure 4-substituted riboses; also for preparing saccharinic acids and lactones via Amadori rearrangement for use as synthons toward herbicidal esters and branched nucleosides.

Technology Process of 3,4-Dihydroxy-5-(hydroxymethyl)-3-methyloxolan-2-one

There total 35 articles about 3,4-Dihydroxy-5-(hydroxymethyl)-3-methyloxolan-2-one 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: 100.0%

5-O-benzyl-2-C-methyl lyxonolactone (86204-15-1,86204-16-2) → (3S,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-3-methyl-dihydro-furan-2-one (492-30-8,7306-56-1,19774-08-4,36791-96-5,36791-97-6,53008-90-5,53008-96-1,53008-97-2,86204-17-3,86204-18-4,93636-22-7)

Guidance literature:

With palladium on activated charcoal; hydrogen;

DOI:10.1246/cl.1983.595

Reference yield: 89.0%

5-O-Triphenylmethyl-2-C-methyl-D-ribono-1,4-lactone (157666-05-2) → 2-C-methyl-D-ribono-1,4-lactone (492-30-8,7306-56-1,19774-08-4,36791-96-5,36791-97-6,53008-90-5,53008-96-1,53008-97-2,86204-17-3,86204-18-4,93636-22-7)

Guidance literature:

With trifluoroacetic acid; In ethyl acetate; for 3h;

Reference yield: 61.4%

N-Benzyl-1-methylamino-1-deoxy-β-D-arabino-2-hexulopyranose (68826-00-6) → 2-C-methyl-D-ribono-1,4-lactone (492-30-8,7306-56-1,19774-08-4,36791-96-5,36791-97-6,53008-90-5,53008-96-1,53008-97-2,86204-17-3,86204-18-4,93636-22-7)

Guidance literature:

N-Benzyl-1-methylamino-1-deoxy-β-D-arabino-2-hexulopyranose; With sodium methylate; copper dichloride; In tetrahydrofuran; methanol; at 20 - 40 ℃; for 3h;

In tetrahydrofuran; methanol; at 23 ℃; for 1h;

upstream raw materials:

D-glucose

5-O-Triphenylmethyl-2-C-methyl-D-ribono-1,4-lactone

N,N-dibenzyl-1-amino-1-deoxy-D-fructose

sodium cyanide

Downstream raw materials:

2-C-Methyl-D-ribose-N-benzyl-N-phenylhydrazon

2-methyl-2,3-O-(1-methylethylidene)-D-ribonic acid γ-lactone

2,3-O-isopropylidene-2-C-methyl-DL-lyxono-1,4-lactone

2,3-O-isopropylidene-2-C-methyl-DL-ribono-1,4-lactone

Refernces

• 1、 -. "METHOD FOR PRODUCING LACTONE". Paragraph 0028; 0033; 0036. . Retrieved 2017/03/24.
• 2、 Naus, Petr,Perlikova, Pavla,Pohl, Radek,Hocek, Michal. "Sugar-modified derivatives of cytostatic 6-(het)aryl-7-deazapurine nucleosides: 2′-c-methylribonucleosides, arabinonucleosides and 2′-deoxy-2′-fluoroarabinonucleosides". scheme or table. p. 957 - 988. Retrieved 2012/06/16.