(2S,3S)-2-Methyl-1,3-pentanediol

Base Information

• Chemical Name: (2S,3S)-2-Methyl-1,3-pentanediol
• CAS No.: 94953-91-0
• Molecular Formula: C₆H₁₄O₂
• Molecular Weight: 118.176
• UNII: 72578O8953
• Nikkaji Number: J1.184.349B
• Wikidata: Q27896253
• Mol file: 94953-91-0.mol

Synonyms:(2S,3S)-2-Methyl-1,3-pentanediol;(2S,3S)-2-Methylpentane-1,3-diol;2-Methyl-1,3-pentanediol, (S,S)-;2-Methyl-1,3-pentanediol, (2S,3S)-;1,3-Pentanediol, 2-methyl-, (2S,3S)-;2-Methyl-1,3-pentanediol, (S,S)-(+)-;94953-91-0;1,3-Pentanediol, 2-methyl-, (S-(R*,R*))-;UNII-72578O8953;72578O8953;AKOS006371769;Q27896253

Chemical Property of (2S,3S)-2-Methyl-1,3-pentanediol

Chemical Property:

• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 118.099379685
• Heavy Atom Count: 8
• Complexity: 54.5

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC(C(C)CO)O
• Isomeric SMILES: CC[C@@H]([C@@H](C)CO)O

Technology Process of (2S,3S)-2-Methyl-1,3-pentanediol

There total 25 articles about (2S,3S)-2-Methyl-1,3-pentanediol 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: 88.0%

(2R,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-2-methylpentan-1-one (952487-49-9) → (2S,3S)-2-methylpentane-1,3-diol (149-31-5,94339-79-4,103729-83-5,103729-87-9,121054-24-8,121054-26-0,94953-91-0)

Guidance literature:

With methanol; sodium tetrahydroborate; at 0 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.tetasy.2011.11.013

Reference yield: 88.0%

[2R,3S]-(-)-3-hydroxy-2-methylpentanoic acid (77302-11-5) → (2S,3S)-2-methylpentane-1,3-diol (149-31-5,94339-79-4,103729-83-5,103729-87-9,121054-24-8,121054-26-0,94953-91-0)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 0 - 21 ℃; for 5h;

DOI:10.1016/S0040-4020(01)86986-6

Reference yield:

propionaldehyde (123-38-6) → (2S,3R)-2-methylpentane-1,3-diol (94339-79-4) + (2R,3R)-2-methylpentane-1,3-diol (261614-97-5) + (2S,3S)-2-methylpentane-1,3-diol (149-31-5,94339-79-4,103729-83-5,103729-87-9,121054-24-8,121054-26-0,94953-91-0) + (2R,3S)-2-methylpentane-1,3-diol (208766-56-7)

Guidance literature:

propionaldehyde; With water; at 20 ℃; for 3h;

With sodium tetrahydroborate; In methanol; at 0 ℃; for 1h; Further stages. Title compound not separated from byproducts.;

DOI:10.1039/b702559a

upstream raw materials:

[2R,3S]-(-)-3-hydroxy-2-methylpentanoic acid

(3S,4S,5E)-4-Methyl-5-hepten-3-ol

(2S,3S)-threo-2-methylpentane-1,3-diol 1-benzyl ether 3-THP ether

(2R,3S)-3-Hydroxy-2-methyl-pentanoic acid (1R,2S)-2-[methyl-(1,2,3,4,5,6,7,8-octahydro-anthracene-9-sulfonyl)-amino]-1-phenyl-propyl ester

Downstream raw materials:

(2S,3S)-2-methyl-1-(4-methylbenzenesulfonyloxy)-3-pentanol

(2S,3S)-3-O-acetyl-2-methyl-1-O-p-toluenesulfonyl-1,3-pentanediol

(4R,6S,7S)-7-hydroxy-4,6-dimethyl-3-nonanone

(-)-serricornin