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

Base Information

• Chemical Name: n-pentenyl 4-O-tert-butyldimethylsilyl-3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside
• CAS No.: 385422-18-4
• Molecular Formula: C₃₆H₅₄O₇Si
• Molecular Weight: 626.906
• Mol file: 385422-18-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about n-pentenyl 4-O-tert-butyldimethylsilyl-3,6-di-O-benzyl-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: 89.0%

n-Pent-4-enyl alcohol (821-09-0) + dibutyl 4-O-tert-butyldimethylsilyl-3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside phosphate (253683-26-0) → n-pentenyl 4-O-tert-butyldimethylsilyl-3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside (385422-18-4)

Guidance literature:

With t-butyldimethylsiyl triflate; In dichloromethane; at -78 ℃; for 0.5h;

DOI:10.1021/jo015987h

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → n-pentenyl 4-O-tert-butyldimethylsilyl-3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside (385422-18-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lutidine / CH₂Cl₂ / 0.25 h / 0 °C

1.2: 87 percent / CH₂Cl₂ / 0.5 h / 0 °C

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

2.2: CH₂Cl₂ / 0.25 h / -78 °C

2.3: 78 percent / DMAP / CH₂Cl₂ / 2 h / 20 °C

3.1: 89 percent / TBSOTf / CH₂Cl₂ / 0.5 h / -78 °C

With lutidine; t-butyldimethylsiyl triflate; 3,3-dimethyldioxirane; In dichloromethane; acetone;

DOI:10.1021/jo015987h

Reference yield:

3,6-di-O-benzyl-D-glucal (145852-76-2) → n-pentenyl 4-O-tert-butyldimethylsilyl-3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside (385422-18-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lutidine / CH₂Cl₂ / 0.25 h / 0 °C

1.2: 87 percent / CH₂Cl₂ / 0.5 h / 0 °C

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

2.2: CH₂Cl₂ / 0.25 h / -78 °C

2.3: 78 percent / DMAP / CH₂Cl₂ / 2 h / 20 °C

3.1: 89 percent / TBSOTf / CH₂Cl₂ / 0.5 h / -78 °C

With lutidine; t-butyldimethylsiyl triflate; 3,3-dimethyldioxirane; In dichloromethane; acetone;

DOI:10.1021/jo015987h

upstream raw materials:

n-Pent-4-enyl alcohol

dibutyl 4-O-tert-butyldimethylsilyl-3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside phosphate

t-butyldimethylsiyl triflate

3,6-di-O-benzyl-D-glucal

Downstream raw materials:

n-pentenyl 4,6-di-O-benzyl-3-O-levulinyl-2-O-pivaloyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside

n-pentenyl 4,6-di-O-benzyl-2-O-pivaloyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside

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