(4R)-3-[(2R,3S,4S)-2,4-Dimethyl-3-hydroxy-5-(benzyloxy)pentanoyl]-4-benzyloxazolidine-2-one

Base Information

Chemical Name:(4R)-3-[(2R,3S,4S)-2,4-Dimethyl-3-hydroxy-5-(benzyloxy)pentanoyl]-4-benzyloxazolidine-2-one
CAS No.:183506-80-1
Molecular Formula:C₂₄H₂₉NO₅
Molecular Weight:411.498
Hs Code.:
DSSTox Substance ID:DTXSID701111344
Nikkaji Number:J1.764.165D

Synonyms:DTXSID701111344;(4R)-3-[(2R,3S,4S)-2,4-Dimethyl-3-hydroxy-5-(benzyloxy)pentanoyl]-4-benzyloxazolidine-2-one;183506-80-1;2,4-Dideoxy-2,4-dimethyl-5-O-(phenylmethyl)-1-C-[(4R)-4-(phenylmethyl)-2-oxo-3-oxazolidinyl]-L-arabinose

Suppliers and Price of (4R)-3-[(2R,3S,4S)-2,4-Dimethyl-3-hydroxy-5-(benzyloxy)pentanoyl]-4-benzyloxazolidine-2-one

Supply Marketing:

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

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Chemical Property of (4R)-3-[(2R,3S,4S)-2,4-Dimethyl-3-hydroxy-5-(benzyloxy)pentanoyl]-4-benzyloxazolidine-2-one

Chemical Property:

XLogP3:3.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:9
Exact Mass:411.20457303
Heavy Atom Count:30
Complexity:556

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Canonical SMILES:CC(COCC1=CC=CC=C1)C(C(C)C(=O)N2C(COC2=O)CC3=CC=CC=C3)O
Isomeric SMILES:C[C@@H](COCC1=CC=CC=C1)[C@@H]([C@@H](C)C(=O)N2[C@@H](COC2=O)CC3=CC=CC=C3)O

Technology Process of (4R)-3-[(2R,3S,4S)-2,4-Dimethyl-3-hydroxy-5-(benzyloxy)pentanoyl]-4-benzyloxazolidine-2-one

There total 5 articles about (4R)-3-[(2R,3S,4S)-2,4-Dimethyl-3-hydroxy-5-(benzyloxy)pentanoyl]-4-benzyloxazolidine-2-one 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: 97.0%

: 79027-28-4
(2S)-3-(benzyloxy)-2-methylpropanal

: 101711-78-8,131685-53-5
(3R)-3-propionyl-4-benzyloxazolidin-2-one

: 183506-80-1
(4R,2'R,3'S,4'S)-4-benzyl-3-(5'-benzyloxy-3'-hydroxy-2',4'-dimethylpentanoyl)-2-oxazolidinone

Guidance literature:: With (-)-sparteine; In dichloromethane; at 0 ℃; for 1.5h;
DOI:10.1016/j.tetlet.2006.09.004

Reference yield: 83.0%

: 63930-49-4
(R)-3-(benzyloxy)-2-methylpropan-1-ol

: 183506-80-1
(4R,2'R,3'S,4'S)-4-benzyl-3-(5'-benzyloxy-3'-hydroxy-2',4'-dimethylpentanoyl)-2-oxazolidinone

Guidance literature:: (R)-3-(benzyloxy)-2-methylpropan-1-ol; With oxalyl dichloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; dimethyl sulfoxide; at -78 - 0 ℃; for 1.5h; Inert atmosphere;

(3R)-3-propionyl-4-benzyloxazolidin-2-one; With di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; In dichloromethane; dimethyl sulfoxide; at -78 - 0 ℃; for 3.5h; Inert atmosphere;
DOI:10.1039/c6ob01583b

Reference yield:

: 81927-55-1
O-benzyl 2,2,2-trichloroacetimidate

: 183506-80-1
(4R,2'R,3'S,4'S)-4-benzyl-3-(5'-benzyloxy-3'-hydroxy-2',4'-dimethylpentanoyl)-2-oxazolidinone

Guidance literature:: Multi-step reaction with 4 steps

1.1: 94 percent / triflic acid / cyclohexane; CH₂Cl₂ / 3 h / 20 °C

2.1: 96 percent / LiBH₄ / tetrahydrofuran; methanol / 2 h

3.1: 97 percent / DMSO; oxalyl chloride / CH₂Cl₂ / 1 h / -78 °C

4.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / 1.5 h / -78 - 0 °C

4.2: 81 percent / CH₂Cl₂ / 2 h / -78 - -10 °C

With lithium borohydride; oxalyl dichloride; trifluorormethanesulfonic acid; di-n-butylboryl trifluoromethanesulfonate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; cyclohexane; 3.1: Swern oxidation;
DOI:10.1016/S0957-4166(02)00178-7