thioethyl 3,4-di-O-benzyl-6-O-4'-oxo-5'-phenyl-valeryl-2-pivaloyl-β-D-glucopyranoside

Base Information

Chemical Name:thioethyl 3,4-di-O-benzyl-6-O-4'-oxo-5'-phenyl-valeryl-2-pivaloyl-β-D-glucopyranoside
CAS No.:449777-93-9
Molecular Formula:C₃₈H₄₆O₈S
Molecular Weight:662.844
Hs Code.:

Synonyms:thioethyl 3,4-di-O-benzyl-6-O-4'-oxo-5'-phenyl-valeryl-2-pivaloyl-β-D-glucopyranoside

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Chemical Property of thioethyl 3,4-di-O-benzyl-6-O-4'-oxo-5'-phenyl-valeryl-2-pivaloyl-β-D-glucopyranoside

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Technology Process of thioethyl 3,4-di-O-benzyl-6-O-4'-oxo-5'-phenyl-valeryl-2-pivaloyl-β-D-glucopyranoside

There total 7 articles about thioethyl 3,4-di-O-benzyl-6-O-4'-oxo-5'-phenyl-valeryl-2-pivaloyl-β-D-glucopyranoside 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:

: 3282-30-2
pivaloyl chloride

: 4-Oxo-5-phenyl-pentanoic acid (2R,3R,4R)-3,4-bis-benzyloxy-6-ethylsulfanyl-5-hydroxy-tetrahydro-pyran-2-ylmethyl ester

: 449777-93-9
thioethyl 3,4-di-O-benzyl-6-O-4'-oxo-5'-phenyl-valeryl-2-pivaloyl-β-D-glucopyranoside

Guidance literature:: With dmap; In dichloromethane; at 20 ℃;
DOI:10.1021/ol026276o

Reference yield:

: 100-39-0
benzyl bromide

: 449777-93-9
thioethyl 3,4-di-O-benzyl-6-O-4'-oxo-5'-phenyl-valeryl-2-pivaloyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: sodium hydride / dimethylformamide / 12 h / 20 °C

2: 5.73 g / TBAF; acetic acid / tetrahydrofuran / 4 h / 20 °C

3: 71 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH₂Cl₂ / 14 h / 20 °C

4: dimethyldioxirane / CH₂Cl₂; acetone / 0.25 h / 0 °C

5: trifluoroacetic anhydride / CH₂Cl₂ / -78 - 20 °C

6: 0.215 g / 4-(dimethylamino)pyridine / CH₂Cl₂ / 20 °C

With dmap; tetrabutyl ammonium fluoride; 3,3-dimethyldioxirane; sodium hydride; acetic acid; dicyclohexyl-carbodiimide; trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1021/ol026276o

Reference yield:

: 58871-10-6
3,4-di-O-benzyl-D-glucal

: 449777-93-9
thioethyl 3,4-di-O-benzyl-6-O-4'-oxo-5'-phenyl-valeryl-2-pivaloyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 71 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH₂Cl₂ / 14 h / 20 °C

2: dimethyldioxirane / CH₂Cl₂; acetone / 0.25 h / 0 °C

3: trifluoroacetic anhydride / CH₂Cl₂ / -78 - 20 °C

4: 0.215 g / 4-(dimethylamino)pyridine / CH₂Cl₂ / 20 °C

With dmap; 3,3-dimethyldioxirane; dicyclohexyl-carbodiimide; trifluoroacetic anhydride; In dichloromethane; acetone;
DOI:10.1021/ol026276o