(S)-2-Hydroxyisovaleric acid allyl ester

Base Information

• Chemical Name: (S)-2-Hydroxyisovaleric acid allyl ester
• CAS No.: 178113-56-9
• Molecular Formula: C8H14O3
• Molecular Weight: 158.197
• DSSTox Substance ID: DTXSID30454178
• Nikkaji Number: J733.400A
• Wikidata: Q82275540
• Mol file: 178113-56-9.mol

Synonyms:(S)-2-Hydroxyisovaleric acid allyl ester;178113-56-9;SCHEMBL12191482;DTXSID30454178;prop-2-enyl (2S)-2-hydroxy-3-methylbutanoate

Chemical Property of (S)-2-Hydroxyisovaleric acid allyl ester

Chemical Property:

• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 158.094294304
• Heavy Atom Count: 11
• Complexity: 140

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(C(=O)OCC=C)O
• Isomeric SMILES: CC(C)[C@@H](C(=O)OCC=C)O

Technology Process of (S)-2-Hydroxyisovaleric acid allyl ester

There total 1 articles about (S)-2-Hydroxyisovaleric acid allyl ester 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:

allyl alcohol (107-18-6) + 5-isopropyl-[1,3]dioxolane-2,4-dione (421545-80-4) → (R)-allyl-2-hydroxy-3-methylbutanoate + (R)-2-Hydroxy-3-methylbutyric acid (17407-56-6) + (S)-2-Hydroxy-3-methylbutanoic acid (17407-55-5) + L-2-hydroxy-3-methylbutanoic acid allyl ester (178113-56-9)

Guidance literature:

allyl alcohol; 5-isopropyl-[1,3]dioxolane-2,4-dione; With hydroquinidine anthraquinone-1,4-diyl diether; In diethyl ether; at -78 ℃; for 6h;

With water; Further stages. Title compound not separated from byproducts.;

DOI:10.1021/ja0255047

Reference yield: 100.0%

(S)-N-(benzyloxycarbonyl)valine (1149-26-4) + L-2-hydroxy-3-methylbutanoic acid allyl ester (178113-56-9) → C21H29NO6

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.tetlet.2014.09.047

Reference yield: 94.0%

4-(benzyloxy)butanoic acid (10385-30-5) + L-2-hydroxy-3-methylbutanoic acid allyl ester (178113-56-9) → allyl (S)-2-{[4-(Benzyloxy)butanoyl]oxy}-3-methylbutanoate

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20 ℃; for 8h; Inert atmosphere;

DOI:10.1002/ejoc.201500677

upstream raw materials:

allyl alcohol

5-isopropyl-[1,3]dioxolane-2,4-dione

Downstream raw materials:

(2S,3R)-3-[(3R,4S)-4-(tert-Butoxycarbonyl-methyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-allyloxycarbonyl-2-methyl-propyl ester

(3S,4R)-4-Benzyloxycarbonylamino-5-methyl-3-triisopropylsilanyloxy-hexanoic acid (S)-1-allyloxycarbonyl-2-methyl-propyl ester

(3S,4R,5S)-4-Benzyloxycarbonylamino-5-methyl-3-triisopropylsilanyloxy-heptanoic acid (S)-1-allyloxycarbonyl-2-methyl-propyl ester

C₅₃H₈₉N₅SiO₁₂

Refernces