Pentanoic acid, 3-oxo-5-(phenylmethoxy)-, 2-methylpropyl ester

Base Information

• Chemical Name: Pentanoic acid, 3-oxo-5-(phenylmethoxy)-, 2-methylpropyl ester
• CAS No.: 106064-33-9
• Molecular Formula: C16H22O4
• Molecular Weight: 278.348
• DSSTox Substance ID: DTXSID30451425
• Wikidata: Q82271445
• Mol file: 106064-33-9.mol

Synonyms:106064-33-9;Pentanoic acid, 3-oxo-5-(phenylmethoxy)-, 2-methylpropyl ester;DTXSID30451425

Chemical Property of Pentanoic acid, 3-oxo-5-(phenylmethoxy)-, 2-methylpropyl ester

Chemical Property:

• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 10
• Exact Mass: 278.15180918
• Heavy Atom Count: 20
• Complexity: 293

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)COC(=O)CC(=O)CCOCC1=CC=CC=C1

Technology Process of Pentanoic acid, 3-oxo-5-(phenylmethoxy)-, 2-methylpropyl ester

There total 1 articles about Pentanoic acid, 3-oxo-5-(phenylmethoxy)-, 2-methylpropyl 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: 70.0%

Benzyloxymethyl chloride (3587-60-8) + isobutyl acetoacetate (7779-75-1) → isobutyl 5-(benzyloxy)-3-oxopentanoate (106064-33-9)

Guidance literature:

isobutyl acetoacetate; With sodium hydride; In tetrahydrofuran;

With n-butyllithium;

Benzyloxymethyl chloride;

DOI:10.1021/ja062364i

Reference yield: 100.0%

isobutyl 5-(benzyloxy)-3-oxopentanoate (106064-33-9) → isobutyl (3R)-5-benzyloxy-3-hydroxypentanoate (912805-56-2)

Guidance literature:

With hydrogen; Ru₂Cl₂[(R)-BINAP]2*Et₃N; In methanol; at 23 ℃; for 66h; under 42923.3 Torr;

DOI:10.1021/ja062364i

Reference yield: 99.0%

isobutyl 5-(benzyloxy)-3-oxopentanoate (106064-33-9) → isobutyl (3S)-5-benzyloxy-3-hydroxypentanoate (106064-44-2)

Guidance literature:

With hydrogen; Ru₂Cl₄-(S)-(2,2'-bis(diphenylphosphino)-1,1'-binaphthyl)2*NEt₃; In methanol; for 60h; under 2585.74 Torr;

DOI:10.1021/jo0503862

upstream raw materials:

Benzyloxymethyl chloride

isobutyl acetoacetate

Downstream raw materials:

isobutyl 5-(benzyloxy)-3-hydroxypentanoate

isobutyl (3S)-5-benzyloxy-3-hydroxypentanoate

isobutyl (3R)-5-benzyloxy-3-hydroxypentanoate

(R)-(+)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)pentanal

Refernces

• 1、 Brooks, Dee W.,Kellogg, Rosemary P.,Cooper, Curt S.. "Substrate modification as a means of enhancing the enantioselectivity of microbial reductions of β-keto esters. An (R)- or (S )-1,3,5-trihydroxypentane synthon". . p. 192 - 196. Retrieved 2007/10/02.