tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleoylamido-glucopyranoside

Base Information

• Chemical Name: tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleoylamido-glucopyranoside
• CAS No.: 216877-47-3
• Molecular Formula: C₃₂H₄₃NO₇Si
• Molecular Weight: 581.781
• Mol file: 216877-47-3.mol

Synonyms:tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleoylamido-glucopyranoside

Chemical Property of tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleoylamido-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleoylamido-glucopyranoside

There total 10 articles about tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleoylamido-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: 73.0%

benzyl bromide (100-39-0) + tert-butyldimethylsilyl 2-deoxy-2-dimethylmaleoyl-β-D-glucopyranoside (216877-35-9) → tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleoylamido-glucopyranoside (216877-47-3)

Guidance literature:

With di(n-butyl)tin oxide;

DOI:10.1021/jo035583k

Reference yield:

tert-butyldimethylsilyl 3,4,6-tri-O-acetyl-2-deoxy-2-dimethylmaleoyl-β-D-glucopyranoside (216876-40-3) → tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleoylamido-glucopyranoside (216877-47-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 73 percent / NaOMe

2: 73 percent / Bu₂SnO

With sodium methylate; di(n-butyl)tin oxide;

DOI:10.1021/jo035583k

Reference yield:

C12H17NO7 → tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleoylamido-glucopyranoside (216877-47-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: pyridine / 20 h / 20 °C

2.1: hydrazine hydrate / N,N-dimethyl-formamide / 23 °C

3.1: 1H-imidazole / dichloromethane / 16 h / 23 °C

4.1: sodium methylate / methanol / 23 °C

5.1: di(n-butyl)tin oxide / toluene / 12 h / Reflux

5.2: 3 h / Reflux

With pyridine; 1H-imidazole; sodium methylate; di(n-butyl)tin oxide; hydrazine hydrate; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

upstream raw materials:

benzyl bromide

tert-butyldimethylsilyl 2-deoxy-2-dimethylmaleoyl-β-D-glucopyranoside

2-deoxy-2-amino glucose

tert-butyldimethylsilyl 3,4,6-tri-O-acetyl-2-deoxy-2-dimethylmaleoyl-β-D-glucopyranoside

Downstream raw materials:

tert-butyldimethylsilyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside

tert-butyldimethylsilyl 3,4,6-tri-O-acetyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside

tert-butyldimethylsilyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside

O-<(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl> trichloroacetimidate