Acetic acid, [[(1R)-1-[(phenylmethoxy)methyl]-2-propenyl]oxy]-

Base Information

Chemical Name:Acetic acid, [[(1R)-1-[(phenylmethoxy)methyl]-2-propenyl]oxy]-
CAS No.:661490-54-6
Molecular Formula:C13H16O4
Molecular Weight:236.268
Hs Code.:
DSSTox Substance ID:DTXSID60465116
Wikidata:Q82290823

Synonyms:661490-54-6;Acetic acid, [[(1R)-1-[(phenylmethoxy)methyl]-2-propenyl]oxy]-;DTXSID60465116

Suppliers and Price of Acetic acid, [[(1R)-1-[(phenylmethoxy)methyl]-2-propenyl]oxy]-

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of Acetic acid, [[(1R)-1-[(phenylmethoxy)methyl]-2-propenyl]oxy]-

Chemical Property:

XLogP3:1.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:8
Exact Mass:236.10485899
Heavy Atom Count:17
Complexity:234

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:C=CC(COCC1=CC=CC=C1)OCC(=O)O
Isomeric SMILES:C=C[C@H](COCC1=CC=CC=C1)OCC(=O)O

Technology Process of Acetic acid, [[(1R)-1-[(phenylmethoxy)methyl]-2-propenyl]oxy]-

There total 2 articles about Acetic acid, [[(1R)-1-[(phenylmethoxy)methyl]-2-propenyl]oxy]- 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%

: 93553-66-3,109613-59-4,114819-44-2,113426-94-1
(2R)-1-(benzyloxy)but-3-en-2-ol

: 79-08-3
bromoacetic acid

: 661490-54-6
((R)-1-Benzyloxymethyl-allyloxy)-acetic acid

Guidance literature:: With sodium hydride; In tetrahydrofuran;

Reference yield:

: 14618-80-5
(R)-benzyl glycidol

: 661490-54-6
((R)-1-Benzyloxymethyl-allyloxy)-acetic acid

Guidance literature:: Multi-step reaction with 2 steps

1.1: n-BuLi / tetrahydrofuran / -10 - 25 °C

2.1: NaH / tetrahydrofuran / 1 h / 0 °C

2.2: tetrahydrofuran / 0 - 20 °C

With n-butyllithium; sodium hydride; In tetrahydrofuran;
DOI:10.1021/ja0455852

Reference yield:

: 661490-54-6
((R)-1-Benzyloxymethyl-allyloxy)-acetic acid

: 790698-11-2
3-[7-(5-(S)-{1-(S),4-(R)-bis-methoxymethoxy-4-[5-(R)-(1-(R)-methoxymethoxy-tridecyl)tetrahydrofuran-2-(R)-yl]butyl}tetrahydrofuran-2-(S)-yl)-2-(R)-(4-methoxybenzyloxy)hept-3-en-5-ynyl]-5-(S)-methyl-5H-furan-2-one

Guidance literature:: Multi-step reaction with 15 steps

1.1: Et₃N; pivaloyl chloride / diethyl ether / 1 h / 0 °C

1.2: n-BuLi / tetrahydrofuran; hexane; diethyl ether / 2 h / 0 °C

2.1: 74 percent / TiCl₄; i-Pr₂NEt; N-methyl-2-pyrrolidinone / CH₂Cl₂ / -78 - -40 °C

3.1: 91 percent / 4-(dimethylamino)-pyridine; DIEA / CH₂Cl₂ / 72 h / 20 °C

4.1: 95 percent / LiBH₄; MeOH / diethyl ether / 2 h / 0 °C

5.1: oxalyl chloride; dimethylsulfoxide; Et₃N / CH₂Cl₂ / 0.25 h / -78 - 0 °C

6.1: t-BuOK / tetrahydrofuran; toluene / 1 h / 0 °C

6.2: 90 percent / tetrahydrofuran; toluene / 2 h / 20 °C

7.1: Cl₂(Cy₃P)(IMes)Ru=CHPh / CH₂Cl₂ / 8 h / Heating

8.1: 83 percent / H₂ / Pd/C / ethyl acetate / 12 h

9.1: 0.42 g / oxalyl chloride; dimethylsulfoxide; DIEA / CH₂Cl₂ / -78 - 0 °C

10.1: Zn(OTf)2; (-)-N-methylephedrine; NEt₃ / 4A molecular sieves / toluene / 0.5 h / 20 °C

10.2: 70 percent / toluene

11.1: 97 percent / 4-(dimethylamino)pyridine; DIEA / CH₂Cl₂ / 72 h / 20 °C

12.1: 97 percent / H₂ / Pd/C / ethanol / 36 h

13.1: 0.062 g / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

14.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

14.2: HMPA / tetrahydrofuran; hexane / 0.5 h / -78 °C

14.3: 95 percent / tetrahydrofuran; hexane / 1 h

15.1: 64 percent / Pd(PPh₃)4; CuI; DIEA / tetrahydrofuran / 4 h / 20 °C

With 2,6-dimethylpyridine; 1-methyl-pyrrolidin-2-one; methanol; dmap; copper(l) iodide; lithium borohydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; Cl₂(PCy₃)(N,N'-(Mes)2-imidazolidin-2-yl)Ru=CHC₆H₅; n-butyllithium; oxalyl dichloride; (-)-N-methylephedrine; potassium tert-butylate; hydrogen; pivaloyl chloride; titanium tetrachloride; zinc trifluoromethanesulfonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; 4 A molecular sieve; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; ethyl acetate; toluene; 9.1: Swern oxidation;
DOI:10.1021/ja0455852