methyl 3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyloxy)-(S)-2-(9-fluorenylmethoxycarbonylamino)propanoate

Base Information

• Chemical Name: methyl 3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyloxy)-(S)-2-(9-fluorenylmethoxycarbonylamino)propanoate
• CAS No.: 1384588-41-3
• Molecular Formula: C₅₃H₅₃NO₁₀
• Molecular Weight: 864.005
• Mol file: 1384588-41-3.mol

Synonyms:methyl 3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyloxy)-(S)-2-(9-fluorenylmethoxycarbonylamino)propanoate

Chemical Property of methyl 3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyloxy)-(S)-2-(9-fluorenylmethoxycarbonylamino)propanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyloxy)-(S)-2-(9-fluorenylmethoxycarbonylamino)propanoate

There total 4 articles about methyl 3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyloxy)-(S)-2-(9-fluorenylmethoxycarbonylamino)propanoate 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:

1-methylcyclopropyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside (1384588-29-7) + N-[(9-fluorenylmethoxy)carbonyl]-L-serine methyl ester (82911-78-2) → methyl 3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyloxy)-(S)-2-(9-fluorenylmethoxycarbonylamino)propanoate (1384588-41-3) + methyl 3-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyloxy)-(S)-2-(9-fluorenylmethoxycarbonylamino)propanoate (1384588-38-8)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 - 20 ℃; optical yield given as %de; Inert atmosphere;

DOI:10.1016/j.carres.2012.03.008

Reference yield:

1-phenylcyclopropyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside (1384588-34-4) + N-[(9-fluorenylmethoxy)carbonyl]-L-serine methyl ester (82911-78-2) → methyl 3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyloxy)-(S)-2-(9-fluorenylmethoxycarbonylamino)propanoate (1384588-41-3) + methyl 3-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyloxy)-(S)-2-(9-fluorenylmethoxycarbonylamino)propanoate (1384588-38-8)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 - 20 ℃; optical yield given as %de; Inert atmosphere;

DOI:10.1016/j.carres.2012.03.008

Reference yield:

2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl trichloroacetimidate (90357-89-4) → methyl 3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyloxy)-(S)-2-(9-fluorenylmethoxycarbonylamino)propanoate (1384588-41-3) + methyl 3-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyloxy)-(S)-2-(9-fluorenylmethoxycarbonylamino)propanoate (1384588-38-8)

Guidance literature:

Multi-step reaction with 2 steps

1: boron trifluoride diethyl etherate / dichloromethane / 0 - 20 °C / Inert atmosphere

2: trimethylsilyl trifluoromethanesulfonate / dichloromethane / -78 - 20 °C / Inert atmosphere

With trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; In dichloromethane; 1: Schmidt glycosidation;

DOI:10.1016/j.carres.2012.03.008

upstream raw materials:

1-methylcyclopropyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside

N-[(9-fluorenylmethoxy)carbonyl]-L-serine methyl ester

1-phenylcyclopropyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl trichloroacetimidate