4,6-Di-O-benzoyl-3-O-benzyl-2-deoxy-2-C-(2-O-tert-butyldimethylsilyl-3,4,6-tri-O-benzyl-α-D-mannopyranosylmethyl)-D-mannopyranosyl 2-pyridylsulfide

Base Information

• Chemical Name: 4,6-Di-O-benzoyl-3-O-benzyl-2-deoxy-2-C-(2-O-tert-butyldimethylsilyl-3,4,6-tri-O-benzyl-α-D-mannopyranosylmethyl)-D-mannopyranosyl 2-pyridylsulfide
• CAS No.: 220931-18-0
• Molecular Formula: C₆₆H₇₃NO₁₁SSi
• Molecular Weight: 1116.46
• Mol file: 220931-18-0.mol

Synonyms:4,6-Di-O-benzoyl-3-O-benzyl-2-deoxy-2-C-(2-O-tert-butyldimethylsilyl-3,4,6-tri-O-benzyl-α-D-mannopyranosylmethyl)-D-mannopyranosyl 2-pyridylsulfide

Chemical Property of 4,6-Di-O-benzoyl-3-O-benzyl-2-deoxy-2-C-(2-O-tert-butyldimethylsilyl-3,4,6-tri-O-benzyl-α-D-mannopyranosylmethyl)-D-mannopyranosyl 2-pyridylsulfide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4,6-Di-O-benzoyl-3-O-benzyl-2-deoxy-2-C-(2-O-tert-butyldimethylsilyl-3,4,6-tri-O-benzyl-α-D-mannopyranosylmethyl)-D-mannopyranosyl 2-pyridylsulfide

There total 13 articles about 4,6-Di-O-benzoyl-3-O-benzyl-2-deoxy-2-C-(2-O-tert-butyldimethylsilyl-3,4,6-tri-O-benzyl-α-D-mannopyranosylmethyl)-D-mannopyranosyl 2-pyridylsulfide 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:

2-Sulfanylpyridine (2637-34-5,73018-10-7) + C63H70Cl3NO12Si → 4,6-Di-O-benzoyl-3-O-benzyl-2-deoxy-2-C-(2-O-tert-butyldimethylsilyl-3,4,6-tri-O-benzyl-α-D-mannopyranosylmethyl)-D-mannopyranosyl 2-pyridylsulfide (220931-18-0)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -15 ℃; Yield given;

DOI:10.1002/(SICI)1521-3765(19990201)5:2<430::AID-CHEM430>3.0.CO;2-D

Reference yield:

(2R,3S,4R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3,4-diol (87316-22-1) → 4,6-Di-O-benzoyl-3-O-benzyl-2-deoxy-2-C-(2-O-tert-butyldimethylsilyl-3,4,6-tri-O-benzyl-α-D-mannopyranosylmethyl)-D-mannopyranosyl 2-pyridylsulfide (220931-18-0)

Guidance literature:

Multi-step reaction with 12 steps

1: 1.) Bu₂SnO, 2.) nBu₄NBr / 1.) toluene, reflux, 4 h, 2.) toluene, 20 deg C, 15 h

2: 94 percent / nBuN₄F / tetrahydrofuran / 0.25 h / 20 °C

3: 99 percent / pyridine / 12 h / 0 °C

4: 74 percent / 3 Angstroem molecular sieves, N-iodosuccinimide / acetonitrile / 1.) 20 deg C, 10 min, 2.) 20 deg C, overnight

5: 1.) O₃, 2.) PPh₃ / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂

6: Bu₃SnH, AIBN / benzene / 4 h / Heating

7: 85 percent / SmI₂ / tetrahydrofuran / 0.17 h / 20 °C

8: 99 percent / acetonitrile / Heating

9: 90 percent / Ph₃SnH, AIBN, F₅PhOH / toluene / 2 h / Heating

10: 86 percent / cerium ammonium nitrate, H₂O / acetonitrile / 0.08 h / 20 °C

11: DBU / CH₂Cl₂ / 4 h / 0 °C

12: BF₃*OEt₂ / CH₂Cl₂ / -15 °C

With pyridine; N-iodo-succinimide; samarium diiodide; ammonium cerium(IV) nitrate; 2,2'-azobis(isobutyronitrile); 2,3,4,5,6-pentafluorophenol; 3 A molecular sieve; boron trifluoride diethyl etherate; triphenylstannane; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; water; tri-n-butyl-tin hydride; di(n-butyl)tin oxide; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; In tetrahydrofuran; dichloromethane; toluene; acetonitrile; benzene;

DOI:10.1002/(SICI)1521-3765(19990201)5:2<430::AID-CHEM430>3.0.CO;2-D

Reference yield:

3-O-(1,3-Diphenylprop-2-en-1-yl)-D-glucal (220931-01-1) → 4,6-Di-O-benzoyl-3-O-benzyl-2-deoxy-2-C-(2-O-tert-butyldimethylsilyl-3,4,6-tri-O-benzyl-α-D-mannopyranosylmethyl)-D-mannopyranosyl 2-pyridylsulfide (220931-18-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 99 percent / pyridine / 12 h / 0 °C

2: 74 percent / 3 Angstroem molecular sieves, N-iodosuccinimide / acetonitrile / 1.) 20 deg C, 10 min, 2.) 20 deg C, overnight

3: 1.) O₃, 2.) PPh₃ / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂

4: Bu₃SnH, AIBN / benzene / 4 h / Heating

5: 85 percent / SmI₂ / tetrahydrofuran / 0.17 h / 20 °C

6: 99 percent / acetonitrile / Heating

7: 90 percent / Ph₃SnH, AIBN, F₅PhOH / toluene / 2 h / Heating

8: 86 percent / cerium ammonium nitrate, H₂O / acetonitrile / 0.08 h / 20 °C

9: DBU / CH₂Cl₂ / 4 h / 0 °C

10: BF₃*OEt₂ / CH₂Cl₂ / -15 °C

With pyridine; N-iodo-succinimide; samarium diiodide; ammonium cerium(IV) nitrate; 2,2'-azobis(isobutyronitrile); 2,3,4,5,6-pentafluorophenol; 3 A molecular sieve; boron trifluoride diethyl etherate; triphenylstannane; water; tri-n-butyl-tin hydride; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; In tetrahydrofuran; dichloromethane; toluene; acetonitrile; benzene;

DOI:10.1002/(SICI)1521-3765(19990201)5:2<430::AID-CHEM430>3.0.CO;2-D

upstream raw materials:

2-Sulfanylpyridine

(2R,3S,4R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3,4-diol

3-O-(1,3-Diphenylprop-2-en-1-yl)-D-glucal

4,6-Di-O-benzoyl-3-O-(1,3-diphenylprop-2-en-1-yl)-D-glucal

Downstream raw materials:

4,6-Di-O-benzoyl-3-O-benzyl-2-deoxy-2-C-(2-O-tert-butyldimethylsilyl-3,4,6-tri-O-benzyl-α-D-mannopyranosylmethyl)-D-mannopyranosyl 2-pyridylsulfone