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

Base Information

Chemical Name:dibutyl 3,4-di-O-benzyl-6-O-4'-oxo-5'-phenyl-valeryl-2-O-pivaloyl-D-glucopyranoside phosphate
CAS No.:449777-87-1
Molecular Formula:C₄₄H₅₉O₁₂P
Molecular Weight:810.919
Hs Code.:

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

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

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

There total 7 articles about dibutyl 3,4-di-O-benzyl-6-O-4'-oxo-5'-phenyl-valeryl-2-O-pivaloyl-D-glucopyranoside phosphate 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-(dibutoxy-phosphoryloxy)-5-hydroxy-tetrahydro-pyran-2-ylmethyl ester

: 449777-87-1
dibutyl 3,4-di-O-benzyl-6-O-4'-oxo-5'-phenyl-valeryl-2-O-pivaloyl-D-glucopyranoside phosphate

Guidance literature:: With dmap; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1021/ol026276o

Reference yield:

: 100-39-0
benzyl bromide

: 449777-87-1
dibutyl 3,4-di-O-benzyl-6-O-4'-oxo-5'-phenyl-valeryl-2-O-pivaloyl-D-glucopyranoside phosphate

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: -78 °C

6: 56 mg / 4-(dimethylamino)pyridine / CH₂Cl₂ / 1 h / 20 °C

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

Reference yield:

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

: 449777-87-1
dibutyl 3,4-di-O-benzyl-6-O-4'-oxo-5'-phenyl-valeryl-2-O-pivaloyl-D-glucopyranoside phosphate

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: -78 °C

4: 56 mg / 4-(dimethylamino)pyridine / CH₂Cl₂ / 1 h / 20 °C

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