4-[2-(benzyloxycarbonylamino)ethyl]phenyl 2,4-di-O-methyl-3-O-{4-O-benzyl-2-O-methyl-3-O-[4-O-acetyl-2-O-methyl-3-O-(3-O-benzyl-2-O-chloroacetyl-4-O-methyl-α-D-rhamnopyranoside)-α-L-fucopyranosyl]-α-L-rhamnopyranosyl}-α-L-rhamnopyranoside

Base Information

• Chemical Name: 4-[2-(benzyloxycarbonylamino)ethyl]phenyl 2,4-di-O-methyl-3-O-{4-O-benzyl-2-O-methyl-3-O-[4-O-acetyl-2-O-methyl-3-O-(3-O-benzyl-2-O-chloroacetyl-4-O-methyl-α-D-rhamnopyranoside)-α-L-fucopyranosyl]-α-L-rhamnopyranosyl}-α-L-rhamnopyranoside
• CAS No.: 176039-88-6
• Molecular Formula: C₆₃H₈₂ClNO₂₁
• Molecular Weight: 1224.79
• Mol file: 176039-88-6.mol

Synonyms:4-[2-(benzyloxycarbonylamino)ethyl]phenyl 2,4-di-O-methyl-3-O-{4-O-benzyl-2-O-methyl-3-O-[4-O-acetyl-2-O-methyl-3-O-(3-O-benzyl-2-O-chloroacetyl-4-O-methyl-α-D-rhamnopyranoside)-α-L-fucopyranosyl]-α-L-rhamnopyranosyl}-α-L-rhamnopyranoside

Chemical Property of 4-[2-(benzyloxycarbonylamino)ethyl]phenyl 2,4-di-O-methyl-3-O-{4-O-benzyl-2-O-methyl-3-O-[4-O-acetyl-2-O-methyl-3-O-(3-O-benzyl-2-O-chloroacetyl-4-O-methyl-α-D-rhamnopyranoside)-α-L-fucopyranosyl]-α-L-rhamnopyranosyl}-α-L-rhamnopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-[2-(benzyloxycarbonylamino)ethyl]phenyl 2,4-di-O-methyl-3-O-{4-O-benzyl-2-O-methyl-3-O-[4-O-acetyl-2-O-methyl-3-O-(3-O-benzyl-2-O-chloroacetyl-4-O-methyl-α-D-rhamnopyranoside)-α-L-fucopyranosyl]-α-L-rhamnopyranosyl}-α-L-rhamnopyranoside

There total 6 articles about 4-[2-(benzyloxycarbonylamino)ethyl]phenyl 2,4-di-O-methyl-3-O-{4-O-benzyl-2-O-methyl-3-O-[4-O-acetyl-2-O-methyl-3-O-(3-O-benzyl-2-O-chloroacetyl-4-O-methyl-α-D-rhamnopyranoside)-α-L-fucopyranosyl]-α-L-rhamnopyranosyl}-α-L-rhamnopyranoside 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: 71.0%

4-<2-(benzyloxycarbonylamino)ethyl>phenyl 2,4-di-O-methyl-3-O-<4-O-benzyl-2-O-methyl-3-O-(4-O-acetyl-2-O-methyl-α-L-fucopyranosyl)-α-L-rhamnopyranosyl>-α-L-rhamnopyranoside (146399-72-6) + ethyl 3-O-benzyl-2-O-chloroacetyl-4-O-methyl-1-thio-α-D-rhamnopyranoside (176039-82-0) → 4-[2-(benzyloxycarbonylamino)ethyl]phenyl 2,4-di-O-methyl-3-O-{4-O-benzyl-2-O-methyl-3-O-[4-O-acetyl-2-O-methyl-3-O-(3-O-benzyl-2-O-chloroacetyl-4-O-methyl-α-D-rhamnopyranoside)-α-L-fucopyranosyl]-α-L-rhamnopyranosyl}-α-L-rhamnopyranoside (176039-88-6)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; In diethyl ether; 1,2-dichloro-ethane; at 0 ℃; for 0.25h;

DOI:10.1016/0040-4020(96)00035-X

Reference yield:

benzyl bromide (100-39-0) → 4-[2-(benzyloxycarbonylamino)ethyl]phenyl 2,4-di-O-methyl-3-O-{4-O-benzyl-2-O-methyl-3-O-[4-O-acetyl-2-O-methyl-3-O-(3-O-benzyl-2-O-chloroacetyl-4-O-methyl-α-D-rhamnopyranoside)-α-L-fucopyranosyl]-α-L-rhamnopyranosyl}-α-L-rhamnopyranoside (176039-88-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) dibutyltin oxide, 2.) cesium fluoride / 1.) methanol, reflux, 1.5 h, 2.) DMF, RT, 17 h

2: 95 percent / NaHCO₃ / dimethylformamide / 1.5 h / Ambient temperature

3: 71 percent / NIS, TfOH, molecular sieves 4 Angstroem / 1,2-dichloro-ethane; diethyl ether / 0.25 h / 0 °C

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; di(n-butyl)tin oxide; sodium hydrogencarbonate; cesium fluoride; In diethyl ether; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/0040-4020(96)00035-X

Reference yield:

ethyl 6-deoxy-2,3-O-isopropylidene-1-thio-α-D-mannopyranoside (145124-97-6) → 4-[2-(benzyloxycarbonylamino)ethyl]phenyl 2,4-di-O-methyl-3-O-{4-O-benzyl-2-O-methyl-3-O-[4-O-acetyl-2-O-methyl-3-O-(3-O-benzyl-2-O-chloroacetyl-4-O-methyl-α-D-rhamnopyranoside)-α-L-fucopyranosyl]-α-L-rhamnopyranosyl}-α-L-rhamnopyranoside (176039-88-6)

Guidance literature:

Multi-step reaction with 5 steps

1: NaH / dimethylformamide / 1 h / Ambient temperature

2: 85 percent / acetic acid / H₂O / 18 h / 50 °C

3: 1.) dibutyltin oxide, 2.) cesium fluoride / 1.) methanol, reflux, 1.5 h, 2.) DMF, RT, 17 h

4: 95 percent / NaHCO₃ / dimethylformamide / 1.5 h / Ambient temperature

5: 71 percent / NIS, TfOH, molecular sieves 4 Angstroem / 1,2-dichloro-ethane; diethyl ether / 0.25 h / 0 °C

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; sodium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; acetic acid; cesium fluoride; In diethyl ether; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/0040-4020(96)00035-X

upstream raw materials:

4-<2-(benzyloxycarbonylamino)ethyl>phenyl 2,4-di-O-methyl-3-O-<4-O-benzyl-2-O-methyl-3-O-(4-O-acetyl-2-O-methyl-α-L-fucopyranosyl)-α-L-rhamnopyranosyl>-α-L-rhamnopyranoside

ethyl 3-O-benzyl-2-O-chloroacetyl-4-O-methyl-1-thio-α-D-rhamnopyranoside

benzyl bromide

ethyl 6-deoxy-2,3-O-isopropylidene-1-thio-α-D-mannopyranoside

Downstream raw materials:

4-[2-(benzyloxycarbonylamino)ethyl]phenyl 2,4-di-O-methyl-3-O-{4-O-benzyl-2-O-methyl-3-O-[4-O-acetyl-2-O-methyl-3-O-(3-O-benzyl-4-O-methyl-α-D-rhamnopyranoside)-α-L-fucopyranosyl]-α-L-rhamnopyranosyl}-α-L-rhamnopyranoside