tert-butyldimethylsilyl 6-O-benzyloxycarbonyl-2-deoxy-3-O-hexanoyl-2-[[(2,2,2-trichloroethoxy)carbonyl]amino]-β-D-glucopyranoside

Base Information

• Chemical Name: tert-butyldimethylsilyl 6-O-benzyloxycarbonyl-2-deoxy-3-O-hexanoyl-2-[[(2,2,2-trichloroethoxy)carbonyl]amino]-β-D-glucopyranoside
• CAS No.: 506442-00-8
• Molecular Formula: C₂₉H₄₄Cl₃NO₁₀Si
• Molecular Weight: 701.114
• Mol file: 506442-00-8.mol

Synonyms:tert-butyldimethylsilyl 6-O-benzyloxycarbonyl-2-deoxy-3-O-hexanoyl-2-[[(2,2,2-trichloroethoxy)carbonyl]amino]-β-D-glucopyranoside

Chemical Property of tert-butyldimethylsilyl 6-O-benzyloxycarbonyl-2-deoxy-3-O-hexanoyl-2-[[(2,2,2-trichloroethoxy)carbonyl]amino]-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyldimethylsilyl 6-O-benzyloxycarbonyl-2-deoxy-3-O-hexanoyl-2-[[(2,2,2-trichloroethoxy)carbonyl]amino]-β-D-glucopyranoside

There total 5 articles about tert-butyldimethylsilyl 6-O-benzyloxycarbonyl-2-deoxy-3-O-hexanoyl-2-[[(2,2,2-trichloroethoxy)carbonyl]amino]-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: 69.0%

benzyl chloroformate (501-53-1,94274-21-2) + tert-butyldimethylsilyl 2-deoxy-3-O-hexanoyl-2-[[(2,2,2-trichloroethoxy)carbonyl]amino]-β-D-glucopyranoside (506441-98-1) → tert-butyldimethylsilyl 6-O-benzyloxycarbonyl-2-deoxy-3-O-hexanoyl-2-[[(2,2,2-trichloroethoxy)carbonyl]amino]-β-D-glucopyranoside (506442-00-8)

Guidance literature:

With dmap; In dichloromethane; at 20 ℃;

DOI:10.1021/ja0284456

Reference yield:

n-hexanoic anhydride (2051-49-2) → tert-butyldimethylsilyl 6-O-benzyloxycarbonyl-2-deoxy-3-O-hexanoyl-2-[[(2,2,2-trichloroethoxy)carbonyl]amino]-β-D-glucopyranoside (506442-00-8)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / CH₂Cl₂ / 4 h / 20 °C

2: 4.01 g / PPTS; MeOH / 4 h / Heating

3: 69 percent / DMAP / CH₂Cl₂ / 20 °C

With pyridine; methanol; dmap; pyridinium p-toluenesulfonate; In dichloromethane;

DOI:10.1021/ja0284456

Reference yield:

tert-butyldimethylsilyl 2-deoxy-2-[[(2,2,2-trichloroethoxy)carbonyl]amino]-β-D-glucopyranoside → tert-butyldimethylsilyl 6-O-benzyloxycarbonyl-2-deoxy-3-O-hexanoyl-2-[[(2,2,2-trichloroethoxy)carbonyl]amino]-β-D-glucopyranoside (506442-00-8)

Guidance literature:

Multi-step reaction with 4 steps

1: PPTS / CH₂Cl₂ / 4 h / Heating

2: pyridine / CH₂Cl₂ / 4 h / 20 °C

3: 4.01 g / PPTS; MeOH / 4 h / Heating

4: 69 percent / DMAP / CH₂Cl₂ / 20 °C

With pyridine; methanol; dmap; pyridinium p-toluenesulfonate; In dichloromethane;

DOI:10.1021/ja0284456

upstream raw materials:

benzyl chloroformate

tert-butyldimethylsilyl 2-deoxy-3-O-hexanoyl-2-[[(2,2,2-trichloroethoxy)carbonyl]amino]-β-D-glucopyranoside

n-hexanoic anhydride

[(4aR,6S,7R,8R,8aS)-6-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-carbamic acid 2,2,2-trichloro-ethyl ester

Downstream raw materials:

tert-butyldimethylsilyl 4-O-(benzyloxycarbonyl)-6-O-[6-O-(benzyloxycarbonyl)-4-O-[bis(benzyloxy)phosphoryl]-2-deoxy-3-O-hexanoyl-2-(hexanoylamino)-β-D-glucopyranosyl]-2-deoxy-3-O-hexanoyl-2-(hexanoylamino)-β-D-glucopyranoside

tert-butyldimethylsilyl 4-O-(benzyloxycarbonyl)-6-O-[6-O-(benzyloxycarbonyl)-4-O-[bis(benzyloxy)phosphoryl]-2-deoxy-3-O-hexanoyl-2-[[(2,2,2-trichloroethoxy)carbonyl]amino]-β-D-glucopyranosyl]-2-deoxy-3-O-hexanoyl-2-(hexanoylamino)-β-D-glucopyranoside

tert-butyldimethylsilyl 6-O-(benzyloxycarbonyl)-4-O-[bis(benzyloxy)phosphoryl]-2-deoxy-3-O-hexanoyl-2-[[(2,2,2-trichloroethoxy)carbonyl]amino]-β-D-glucopyranoside