methyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-1-thio-α-D-mannopyranoside

Base Information

• Chemical Name: methyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-1-thio-α-D-mannopyranoside
• CAS No.: 344914-63-2
• Molecular Formula: C₆₂H₆₆O₁₀S
• Molecular Weight: 1003.27

Synonyms:methyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-1-thio-α-D-mannopyranoside

Chemical Property of methyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-1-thio-α-D-mannopyranoside

Chemical Property:

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Technology Process of methyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-1-thio-α-D-mannopyranoside

There total 10 articles about methyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-1-thio-α-D-mannopyranoside 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: 85.0%

C13H30SSn + 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α,β-D-mannopyranosyl fluoride (344914-59-6) → methyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-1-thio-α-D-mannopyranoside (344914-63-2) + C62H66O10S

Guidance literature:

C₁₃H₃₀SSn; 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α,β-D-mannopyranosyl fluoride; In tetrahydrofuran; 1,2-dichloro-ethane; at 0 ℃; for 0.0833333h;

With tin(IV) chloride; In 1,2-dichloro-ethane; at 0 ℃; for 0.25h;

With sodium fluoride; In ethyl acetate; for 1h;

DOI:10.1016/S0008-6215(01)00047-7

Reference yield:

p-methoxyphenyl α-D-mannopyranoside (28541-75-5,12167-34-9) → methyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-1-thio-α-D-mannopyranoside (344914-63-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 92 percent / 2,6-di-t-butyl-4-methylpyridne / acetonitrile / 12 h / Heating

2.1: NaH (in oil) / dimethylformamide; petroleum ether / 0.42 h / 20 °C

2.2: dimethylformamide; petroleum ether / 2 h / 0 °C

3.1: 70 percent / AcOH; H₂O / CHCl₃ / 2 h / 80 °C

4.1: 64 percent / 4 Angstroem molecular sieves; phenylselenium chloride; silver trifluoromethanesulfonate / toluene / 0.5 h / -30 °C

5.1: 78 percent / ammonia / CH₂Cl₂; methanol / 36 h / 20 °C

6.1: NaH (in oil) / dimethylformamide / 30 h / 0 °C

6.2: 85 percent / dimethylformamide / 1 h / 20 °C

7.1: 74 percent / Bu₄NPF₆ / acetonitrile; H₂O / 72 h / 25 °C / Electrochemical reaction; Pt electrodes; ref.: Ag/AgCl; 1.55V

8.1: 86 percent / diethylaminosulfur trifluoride / tetrahydrofuran / 0.5 h / -30 - 20 °C

9.1: tetrahydrofuran; 1,2-dichloro-ethane / 0.08 h / 0 °C

9.2: SnCl₄ / 1,2-dichloro-ethane / 0.25 h / 0 °C

9.3: 85 percent / NaF / ethyl acetate / 1 h

With Phenylselenyl chloride; 2,6-di-tert-butyl-4-methylpyridine; diethylamino-sulfur trifluoride; 4 A molecular sieve; ammonia; water; silver trifluoromethanesulfonate; tert-butylammonium hexafluorophosphate(V); sodium hydride; acetic acid; In tetrahydrofuran; methanol; dichloromethane; chloroform; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile; Petroleum ether;

DOI:10.1016/S0008-6215(01)00047-7

Reference yield:

methyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside (129163-10-6) → methyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-1-thio-α-D-mannopyranoside (344914-63-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 64 percent / 4 Angstroem molecular sieves; phenylselenium chloride; silver trifluoromethanesulfonate / toluene / 0.5 h / -30 °C

2.1: 78 percent / ammonia / CH₂Cl₂; methanol / 36 h / 20 °C

3.1: NaH (in oil) / dimethylformamide / 30 h / 0 °C

3.2: 85 percent / dimethylformamide / 1 h / 20 °C

4.1: 74 percent / Bu₄NPF₆ / acetonitrile; H₂O / 72 h / 25 °C / Electrochemical reaction; Pt electrodes; ref.: Ag/AgCl; 1.55V

5.1: 86 percent / diethylaminosulfur trifluoride / tetrahydrofuran / 0.5 h / -30 - 20 °C

6.1: tetrahydrofuran; 1,2-dichloro-ethane / 0.08 h / 0 °C

6.2: SnCl₄ / 1,2-dichloro-ethane / 0.25 h / 0 °C

6.3: 85 percent / NaF / ethyl acetate / 1 h

With Phenylselenyl chloride; diethylamino-sulfur trifluoride; 4 A molecular sieve; ammonia; silver trifluoromethanesulfonate; tert-butylammonium hexafluorophosphate(V); sodium hydride; In tetrahydrofuran; methanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/S0008-6215(01)00047-7

upstream raw materials:

2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α,β-D-mannopyranosyl fluoride

p-methoxyphenyl α-D-mannopyranoside

methyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside

p-methoxyphenyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-mannopyranoside

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