D-erythro-Pentonic acid, 2,3-dideoxy-5-O-[(1,1-dimethylethyl)dimethylsilyl]-2-(phenylmethyl)-, gamma-lactone

Base Information

• Chemical Name: D-erythro-Pentonic acid, 2,3-dideoxy-5-O-[(1,1-dimethylethyl)dimethylsilyl]-2-(phenylmethyl)-, gamma-lactone
• CAS No.: 172649-42-2
• Molecular Formula: C₁₈H₂₈O₃Si
• Molecular Weight: 320.504
• DSSTox Substance ID: DTXSID501111100
• Mol file: 172649-42-2.mol

Synonyms:SCHEMBL15713419;DTXSID501111100;172649-42-2;D-erythro-Pentonic acid, 2,3-dideoxy-5-O-[(1,1-dimethylethyl)dimethylsilyl]-2-(phenylmethyl)-, gamma-lactone

Chemical Property of D-erythro-Pentonic acid, 2,3-dideoxy-5-O-[(1,1-dimethylethyl)dimethylsilyl]-2-(phenylmethyl)-, gamma-lactone

Chemical Property:

• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 320.18077129
• Heavy Atom Count: 22
• Complexity: 380

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)OCC1CC(C(=O)O1)CC2=CC=CC=C2
• Isomeric SMILES: CC(C)(C)[Si](C)(C)OC[C@@H]1C[C@H](C(=O)O1)CC2=CC=CC=C2

Technology Process of D-erythro-Pentonic acid, 2,3-dideoxy-5-O-[(1,1-dimethylethyl)dimethylsilyl]-2-(phenylmethyl)-, gamma-lactone

There total 4 articles about D-erythro-Pentonic acid, 2,3-dideoxy-5-O-[(1,1-dimethylethyl)dimethylsilyl]-2-(phenylmethyl)-, gamma-lactone 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:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6) → dihydro-5(S)-<<(tert-butyldimethylsilyl)oxy>methyl>-3(R)-(phenylmethyl)-3(2H)-furanone (172649-42-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / imidazole / CH₂Cl₂ / 4 h / 0 - 20 °C

2: 1.) LDA / 1.) THF, hexane, 30 min, 2.) THF, hexane, 3 h

With 1H-imidazole; lithium diisopropyl amide; In dichloromethane;

DOI:10.1021/jm00047a001

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → dihydro-5(S)-<<(tert-butyldimethylsilyl)oxy>methyl>-3(R)-(phenylmethyl)-3(2H)-furanone (172649-42-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / imidazole / CH₂Cl₂ / 4 h / 0 - 20 °C

2: 1.) LDA / 1.) THF, hexane, 30 min, 2.) THF, hexane, 3 h

With 1H-imidazole; lithium diisopropyl amide; In dichloromethane;

DOI:10.1021/jm00047a001

Reference yield:

(5S)-(5-tert-butyldimethylsilyloxymethyl)furan-2(5H)-one (62396-80-9) + benzyl bromide (100-39-0) → dihydro-5(S)-<<(tert-butyldimethylsilyl)oxy>methyl>-3(R)-(phenylmethyl)-3(2H)-furanone (172649-42-2)

Guidance literature:

With lithium diisopropyl amide; Yield given. Multistep reaction; 1.) THF, hexane, 30 min, 2.) THF, hexane, 3 h;

DOI:10.1021/jm00047a001

upstream raw materials:

(5S)-(5-tert-butyldimethylsilyloxymethyl)furan-2(5H)-one

benzyl bromide

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

tert-butyldimethylsilyl chloride

Downstream raw materials:

3R,5S-5-Azidomethyl-3-benzyl-4,5-dihydro-2(3H)-furanon

N-(2(R)-hydroxy-1-(S)-indanyl)-2(R)-(phenylmethyl)-4(S)-<(tert-butyldimethylsilyl)oxy>-5-<1-<4-<(1,1-dimethylethoxy)carbonyl>-2(S)-(N-tert-butylcarbamoyl)piperazinyl>>pentanamide

(3S,4aS,8aS)-2-[(2S,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-5-phenyl-pentyl]-decahydro-isoquinoline-3-carboxylic acid tert-butylamide

2(R)-(phenylmethyl)-4(S)-<(tert-butyldimethylsilyl)oxy>-5-<1-<4-<(1,1-dimethylethoxy)carbonyl>-2(S)-(N-tert-butylcarbamoyl)piperazinyl>>pentanoic acid

Refernces

• 1、 -. "INHIBITORS OF CENTRAL NERVOUS SYSTEM VASOACTIVE INHIBITORY PEPTIDE RECEPTOR 2". Page/Page column 5; 18; 58. . Retrieved 2014/05/24.