N-benzyloxycarbonyl-O-4)-(3-O-acetyl-β-D-xylopyranosyl)>-L-serylglycine benzyl ester

Base Information

• Chemical Name: N-benzyloxycarbonyl-O-4)-(3-O-acetyl-β-D-xylopyranosyl)>-L-serylglycine benzyl ester
• CAS No.: 162355-80-8
• Molecular Formula: C₆₁H₅₈N₂O₂₀
• Molecular Weight: 1139.13

Synonyms:

Chemical Property of N-benzyloxycarbonyl-O-4)-(3-O-acetyl-β-D-xylopyranosyl)>-L-serylglycine benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of N-benzyloxycarbonyl-O-4)-(3-O-acetyl-β-D-xylopyranosyl)>-L-serylglycine benzyl ester

There total 8 articles about N-benzyloxycarbonyl-O-4)-(3-O-acetyl-β-D-xylopyranosyl)>-L-serylglycine benzyl ester 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:

N-(Benzyloxycarbonyl)-L-seryl-glycine benzyl ester (2543-27-3) → N-benzyloxycarbonyl-O-4)-(3-O-acetyl-β-D-xylopyranosyl)>-L-serylglycine benzyl ester (162355-80-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 68 percent / molecular sieves 4A, silver triflate / 1,2-dichloro-ethane / 1.5 h / 0 °C

2: 85 percent / thiourea, pyridine / ethanol / 20 h / 80 °C

3: 1.) camphorsulfonic acid, 2.) MeOH / 1.) DMF, 40 deg C, 2.) DMF, 0 deg C, 30 min

4: 75 percent / molecular sieves 4A, trimethylsilyl triflate / CH₂Cl₂; toluene / 0.75 h / -20 °C

5: 94 percent / aq. AcOH / 0.25 h / 100 °C

6: 1.) dibutyltin oxide / 1.) benzene, reflux, 15 h, 2.) benzene, RT, 3 h

With pyridine; methanol; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; camphor-10-sulfonic acid; silver trifluoromethanesulfonate; di(n-butyl)tin oxide; acetic acid; thiourea; In ethanol; dichloromethane; 1,2-dichloro-ethane; toluene;

DOI:10.1016/S0008-6215(00)90973-X

Reference yield:

1,2,3,4-Tetra-O-chloroacetyl-α-D-xylopyranose (128902-75-0) → N-benzyloxycarbonyl-O-4)-(3-O-acetyl-β-D-xylopyranosyl)>-L-serylglycine benzyl ester (162355-80-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 95 percent / titanium(IV) chloride / CH₂Cl₂ / 4 h / Ambient temperature

2: 68 percent / molecular sieves 4A, silver triflate / 1,2-dichloro-ethane / 1.5 h / 0 °C

3: 85 percent / thiourea, pyridine / ethanol / 20 h / 80 °C

4: 1.) camphorsulfonic acid, 2.) MeOH / 1.) DMF, 40 deg C, 2.) DMF, 0 deg C, 30 min

5: 75 percent / molecular sieves 4A, trimethylsilyl triflate / CH₂Cl₂; toluene / 0.75 h / -20 °C

6: 94 percent / aq. AcOH / 0.25 h / 100 °C

7: 1.) dibutyltin oxide / 1.) benzene, reflux, 15 h, 2.) benzene, RT, 3 h

With pyridine; methanol; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; camphor-10-sulfonic acid; silver trifluoromethanesulfonate; titanium tetrachloride; di(n-butyl)tin oxide; acetic acid; thiourea; In ethanol; dichloromethane; 1,2-dichloro-ethane; toluene;

DOI:10.1016/S0008-6215(00)90973-X

Reference yield:

2,3,4-tri-O-chloroacetyl-α-D-xylopyranosyl chloride (162355-87-5) → N-benzyloxycarbonyl-O-4)-(3-O-acetyl-β-D-xylopyranosyl)>-L-serylglycine benzyl ester (162355-80-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 68 percent / molecular sieves 4A, silver triflate / 1,2-dichloro-ethane / 1.5 h / 0 °C

2: 85 percent / thiourea, pyridine / ethanol / 20 h / 80 °C

3: 1.) camphorsulfonic acid, 2.) MeOH / 1.) DMF, 40 deg C, 2.) DMF, 0 deg C, 30 min

4: 75 percent / molecular sieves 4A, trimethylsilyl triflate / CH₂Cl₂; toluene / 0.75 h / -20 °C

5: 94 percent / aq. AcOH / 0.25 h / 100 °C

6: 1.) dibutyltin oxide / 1.) benzene, reflux, 15 h, 2.) benzene, RT, 3 h

With pyridine; methanol; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; camphor-10-sulfonic acid; silver trifluoromethanesulfonate; di(n-butyl)tin oxide; acetic acid; thiourea; In ethanol; dichloromethane; 1,2-dichloro-ethane; toluene;

DOI:10.1016/S0008-6215(00)90973-X

upstream raw materials:

acetic anhydride

N-benzyloxycarbonyl-O-4)-β-D-xylopyranosyl>-L-serylglycine benzyl ester

N-(Benzyloxycarbonyl)-L-seryl-glycine benzyl ester

1,2,3,4-Tetra-O-chloroacetyl-α-D-xylopyranose

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