2-Deoxy-L-threo-pentonic acid gamma-lactone

Base Information

• Chemical Name: 2-Deoxy-L-threo-pentonic acid gamma-lactone
• CAS No.: 78185-09-8
• Molecular Formula: C5H8 O4
• Molecular Weight: 132.116
• Hs Code.: 2932209090
• ChEMBL ID: CHEMBL97916
• Mol file: 78185-09-8.mol

Synonyms:2-Deoxy-L-threo-pentonic acid gamma-lactone;78185-09-8;CHEMBL97916;SCHEMBL24114686

Chemical Property of 2-Deoxy-L-threo-pentonic acid gamma-lactone

Chemical Property:

• PSA: 66.76000
• Density: 1.438
• LogP: -1.34490
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 132.04225873
• Heavy Atom Count: 9
• Complexity: 122

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1=O)CO)O
• Isomeric SMILES: C1[C@@H]([C@@H](OC1=O)CO)O

Technology Process of 2-Deoxy-L-threo-pentonic acid gamma-lactone

There total 14 articles about 2-Deoxy-L-threo-pentonic acid gamma-lactone 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: 93.0%

methyl (4R)-4,5-O-isopropylidene-2-diazo-3,4,5-trihydroxypentanoate → (5R)-4-hydroxymethyltetrahydrofuran-2-one (34371-14-7,38996-12-2,38996-14-4,73209-20-8,78185-08-7,78185-09-8,106357-04-4)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 24h; Ambient temperature;

DOI:10.1016/S0040-4020(01)87898-4

Reference yield: 77.8%

methyl (4R)-4,5-O-isopropylidene-3,4,5-trihydroxypentanoate (74262-77-4,74262-81-0,83159-90-4,83541-52-0,84064-19-7) → (5R)-4-hydroxymethyltetrahydrofuran-2-one (34371-14-7,38996-12-2,38996-14-4,73209-20-8,78185-08-7,78185-09-8,106357-04-4)

Guidance literature:

With trifluoroacetic acid; In water; for 3h;

DOI:10.1016/S0040-4020(01)87898-4

Reference yield: 59.0%

(3RS,4SR)-3,5-Bispentan-1,4-olide → 3,4-trans(erythro)-3,5-dihydroxy-4-pentanolide (34371-14-7,38996-12-2,38996-14-4,73209-20-8,78185-08-7,78185-09-8,106357-04-4)

Guidance literature:

With peracetic acid; sodium acetate; potassium bromide; In acetic acid;

DOI:10.1039/a804282i

upstream raw materials:

methyl (4R)-4,5-O-isopropylidene-3,4,5-trihydroxypentanoate

tert-butyl (4R)-4,5-O-isopropylidene-3,4,5-trihydroxypentanoate

3-(tert-Butyl-dimethyl-silanyloxy)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-propionic acid methyl ester

O,O'-isopropylidene D-glycerinaldehyde

Downstream raw materials:

(5S)-5-(tert-butyldimethylsilanyloxymethyl)-5H-furan-2-one

5-tert-butyldimethylsilyl ether of (4R,5R)-4-hydroxy-5-hydroxymethyltetrahydrofuran-2-one

5-tert-butyldimethylsilyl ether of (4S,5R)-4-hydroxy-5-hydroxymethyltetrahydrofuran-2-one

bis-tert-butyldimethylsilyl ether of (4R,5R)-4-hydroxy-5-hydroxymethyltetrahydrofuran-2-one