tert-butyldimethylsilyl 3,4,6-tri-O-acetyl-2-(benzyloxycarbonyl)amino-2-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: tert-butyldimethylsilyl 3,4,6-tri-O-acetyl-2-(benzyloxycarbonyl)amino-2-deoxy-β-D-glucopyranoside
• CAS No.: 816451-36-2
• Molecular Formula: C₂₆H₃₉NO₁₀Si
• Molecular Weight: 553.682
• Mol file: 816451-36-2.mol

Synonyms:tert-butyldimethylsilyl 3,4,6-tri-O-acetyl-2-(benzyloxycarbonyl)amino-2-deoxy-β-D-glucopyranoside

Chemical Property of tert-butyldimethylsilyl 3,4,6-tri-O-acetyl-2-(benzyloxycarbonyl)amino-2-deoxy-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyldimethylsilyl 3,4,6-tri-O-acetyl-2-(benzyloxycarbonyl)amino-2-deoxy-β-D-glucopyranoside

There total 5 articles about tert-butyldimethylsilyl 3,4,6-tri-O-acetyl-2-(benzyloxycarbonyl)amino-2-deoxy-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: 95.0%

tert-butyldimethylsilyl chloride (18162-48-6) + 3,4,6-tri-O-acetyl-2-{[(benzyloxy)carbonyl]amino}-2-deoxy-β-D-glucopyranose (99194-76-0) → tert-butyldimethylsilyl 3,4,6-tri-O-acetyl-2-(benzyloxycarbonyl)amino-2-deoxy-β-D-glucopyranoside (816451-36-2)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide;

DOI:10.1002/anie.200460388

Reference yield: 95.0%

tert-butyldimethylsilyl chloride (18162-48-6) + 2-benzyloxycarbonylamino-2-deoxy-3,4,6-tri-O-acetyl-D-glucopyranose (99194-76-0,140183-53-5) → tert-butyldimethylsilyl 3,4,6-tri-O-acetyl-2-(benzyloxycarbonyl)amino-2-deoxy-β-D-glucopyranoside (816451-36-2)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 11h;

DOI:10.1002/chem.200501348

Reference yield:

2-(acetoxymethyl)-5-{[(benzyloxy)carbonyl]amino}tetrahydropyran-3,4,6-triyl triacetate (35946-66-8) → tert-butyldimethylsilyl 3,4,6-tri-O-acetyl-2-(benzyloxycarbonyl)amino-2-deoxy-β-D-glucopyranoside (816451-36-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / hydrazine acetate / tetrahydrofuran / 24 h / 20 °C

2: 95 percent / imidazole / dimethylformamide / 11 h / 20 °C

With 1H-imidazole; hydrazinium monoacetate; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1002/chem.200501348

upstream raw materials:

tert-butyldimethylsilyl chloride

3,4,6-tri-O-acetyl-2-{[(benzyloxy)carbonyl]amino}-2-deoxy-β-D-glucopyranose

2-benzyloxycarbonylamino-2-deoxy-3,4,6-tri-O-acetyl-D-glucopyranose

2-(acetoxymethyl)-5-{[(benzyloxy)carbonyl]amino}tetrahydropyran-3,4,6-triyl triacetate

Downstream raw materials:

TBDMS 2-deoxy-2-(N-benzyloxycarbonylamino)-β-D-glucopyranoside

C₃₀H₃₃Cl₃N₂O₁₀

C₃₄H₄₇NO₁₀Si

C₂₉H₄₁NO₈Si