n-pentenyl 3,6-di-O-benzyl-4-O-levulinyl-2-O-pivaloyl-β-D-glucopyranoside

Base Information

Chemical Name:n-pentenyl 3,6-di-O-benzyl-4-O-levulinyl-2-O-pivaloyl-β-D-glucopyranoside
CAS No.:385422-19-5
Molecular Formula:C₃₅H₄₆O₉
Molecular Weight:610.745
Hs Code.:

Synonyms:n-pentenyl 3,6-di-O-benzyl-4-O-levulinyl-2-O-pivaloyl-β-D-glucopyranoside

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Chemical Property of n-pentenyl 3,6-di-O-benzyl-4-O-levulinyl-2-O-pivaloyl-β-D-glucopyranoside

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Technology Process of n-pentenyl 3,6-di-O-benzyl-4-O-levulinyl-2-O-pivaloyl-β-D-glucopyranoside

There total 5 articles about n-pentenyl 3,6-di-O-benzyl-4-O-levulinyl-2-O-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: 88.0%

: 821-09-0
n-Pent-4-enyl alcohol

: 385421-76-1
dibutyl 3,6-di-O-benzyl-4-O-levulinyl-2-O-pivaloyl-β-D-glucopyranosyl phosphate

: 385422-19-5
n-pentenyl 3,6-di-O-benzyl-4-O-levulinyl-2-O-pivaloyl-β-D-glucopyranoside

Guidance literature:: With t-butyldimethylsiyl triflate; In dichloromethane; at -78 ℃; for 0.166667h;
DOI:10.1021/jo015987h

Reference yield:

: 3282-30-2
pivaloyl chloride

: 385422-19-5
n-pentenyl 3,6-di-O-benzyl-4-O-levulinyl-2-O-pivaloyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: dimethyl dioxirane / CH₂Cl₂; acetone / 0.33 h / 0 °C

1.2: CH₂Cl₂ / 0.25 h / -78 °C

1.3: 89 percent / DMAP / CH₂Cl₂ / 2 h / 20 °C

2.1: 88 percent / TBSOTf / CH₂Cl₂ / 0.17 h / -78 °C

With t-butyldimethylsiyl triflate; 3,3-dimethyldioxirane; In dichloromethane; acetone;
DOI:10.1021/jo015987h

Reference yield:

: 123-76-2
levulinic acid

: 385422-19-5
n-pentenyl 3,6-di-O-benzyl-4-O-levulinyl-2-O-pivaloyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: DMAP; diisopropylcarbodiimide / CH₂Cl₂ / 0 °C

1.2: 91 percent / CH₂Cl₂ / 15 h / 2 °C

2.1: dimethyl dioxirane / CH₂Cl₂; acetone / 0.33 h / 0 °C

2.2: CH₂Cl₂ / 0.25 h / -78 °C

2.3: 89 percent / DMAP / CH₂Cl₂ / 2 h / 20 °C

3.1: 88 percent / TBSOTf / CH₂Cl₂ / 0.17 h / -78 °C

With dmap; t-butyldimethylsiyl triflate; 3,3-dimethyldioxirane; diisopropyl-carbodiimide; In dichloromethane; acetone;
DOI:10.1021/jo015987h