4-<2-(benzyloxycarbonylamino)ethyl>phenyl 2,4-di-O-methyl-3-O-<4-O-benzyl-2-O-methyl-3-O-(4-O-acetyl-3-O-chloroacetyl-2-O-methyl-α/β-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-3-O-chloroacetyl-2-O-methyl-α/β-L-fucopyranosyl)-α-L-rhamnopyranosyl>-α-L-rhamnopyranoside
• CAS No.: 146399-70-4
• Molecular Formula: C₄₉H₆₄ClNO₁₇
• Molecular Weight: 974.497

Synonyms:

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-3-O-chloroacetyl-2-O-methyl-α/β-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-3-O-chloroacetyl-2-O-methyl-α/β-L-fucopyranosyl)-α-L-rhamnopyranosyl>-α-L-rhamnopyranoside

There total 9 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-3-O-chloroacetyl-2-O-methyl-α/β-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:

tyrosamine (51-67-2) → 4-<2-(benzyloxycarbonylamino)ethyl>phenyl 2,4-di-O-methyl-3-O-<4-O-benzyl-2-O-methyl-3-O-(4-O-acetyl-3-O-chloroacetyl-2-O-methyl-α/β-L-fucopyranosyl)-α-L-rhamnopyranosyl>-α-L-rhamnopyranoside (146399-70-4,146399-71-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 2N NaOH / H₂O / 18 h

2: 370 mg / NIS, TfOH, MS 4 Angstroem / 1,2-dichloro-ethane; diethyl ether / 0.5 h / 20 °C

3: 304 mg / t-BuOK / methanol / 1 h

4: 575 mg / NIS, TfOH, MS 4 Angstroem / 1,2-dichloro-ethane; diethyl ether / 0.25 h / -30 °C

5: 93 percent / t-BuOK / methanol / 4 h

6: 1) MS 4 Angstroem, 2) NIS, TfOH / 1) 1,2-dichloroethane, Et₂O, -30 deg C, 30 min, 2) 1,2-dichloroethane, Et₂O, 90 min

With sodium hydroxide; N-iodo-succinimide; trifluorormethanesulfonic acid; MS 4 Angstroem; potassium tert-butylate; In methanol; diethyl ether; water; 1,2-dichloro-ethane;

DOI:10.1016/S0040-4020(01)89043-8

Reference yield:

N-benzyloxycarbonyl-2-(4-hydroxyphenyl)ethylamine (29655-46-7) → 4-<2-(benzyloxycarbonylamino)ethyl>phenyl 2,4-di-O-methyl-3-O-<4-O-benzyl-2-O-methyl-3-O-(4-O-acetyl-3-O-chloroacetyl-2-O-methyl-α/β-L-fucopyranosyl)-α-L-rhamnopyranosyl>-α-L-rhamnopyranoside (146399-70-4,146399-71-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 370 mg / NIS, TfOH, MS 4 Angstroem / 1,2-dichloro-ethane; diethyl ether / 0.5 h / 20 °C

2: 304 mg / t-BuOK / methanol / 1 h

3: 575 mg / NIS, TfOH, MS 4 Angstroem / 1,2-dichloro-ethane; diethyl ether / 0.25 h / -30 °C

4: 93 percent / t-BuOK / methanol / 4 h

5: 1) MS 4 Angstroem, 2) NIS, TfOH / 1) 1,2-dichloroethane, Et₂O, -30 deg C, 30 min, 2) 1,2-dichloroethane, Et₂O, 90 min

With N-iodo-succinimide; trifluorormethanesulfonic acid; MS 4 Angstroem; potassium tert-butylate; In methanol; diethyl ether; 1,2-dichloro-ethane;

DOI:10.1016/S0040-4020(01)89043-8

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → 4-<2-(benzyloxycarbonylamino)ethyl>phenyl 2,4-di-O-methyl-3-O-<4-O-benzyl-2-O-methyl-3-O-(4-O-acetyl-3-O-chloroacetyl-2-O-methyl-α/β-L-fucopyranosyl)-α-L-rhamnopyranosyl>-α-L-rhamnopyranoside (146399-70-4,146399-71-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 2N NaOH / H₂O / 18 h

2: 370 mg / NIS, TfOH, MS 4 Angstroem / 1,2-dichloro-ethane; diethyl ether / 0.5 h / 20 °C

3: 304 mg / t-BuOK / methanol / 1 h

4: 575 mg / NIS, TfOH, MS 4 Angstroem / 1,2-dichloro-ethane; diethyl ether / 0.25 h / -30 °C

5: 93 percent / t-BuOK / methanol / 4 h

6: 1) MS 4 Angstroem, 2) NIS, TfOH / 1) 1,2-dichloroethane, Et₂O, -30 deg C, 30 min, 2) 1,2-dichloroethane, Et₂O, 90 min

With sodium hydroxide; N-iodo-succinimide; trifluorormethanesulfonic acid; MS 4 Angstroem; potassium tert-butylate; In methanol; diethyl ether; water; 1,2-dichloro-ethane;

DOI:10.1016/S0040-4020(01)89043-8

upstream raw materials:

ethyl 4-O-acetyl-3-O-chloroacetyl-2-O-methyl-1-thio-β-L-fucopyranoside

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

tyrosamine

N-benzyloxycarbonyl-2-(4-hydroxyphenyl)ethylamine

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-α-L-fucopyranosyl)-α-L-rhamnopyranosyl>-α-L-rhamnopyranoside

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-β-L-fucopyranosyl)-α-L-rhamnopyranosyl>-α-L-rhamnopyranoside

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

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