1,6-anhydro-2-azido-2-deoxy-3-S-(2,4-dinitrophenyl)-4-O-p-methoxybenzyl-3-thio-β-D-galactopyranose

Base Information

• Chemical Name: 1,6-anhydro-2-azido-2-deoxy-3-S-(2,4-dinitrophenyl)-4-O-p-methoxybenzyl-3-thio-β-D-galactopyranose
• CAS No.: 331633-97-7
• Molecular Formula: C₂₀H₁₉N₅O₈S
• Molecular Weight: 489.466
• Mol file: 331633-97-7.mol

Synonyms:1,6-anhydro-2-azido-2-deoxy-3-S-(2,4-dinitrophenyl)-4-O-p-methoxybenzyl-3-thio-β-D-galactopyranose

Chemical Property of 1,6-anhydro-2-azido-2-deoxy-3-S-(2,4-dinitrophenyl)-4-O-p-methoxybenzyl-3-thio-β-D-galactopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,6-anhydro-2-azido-2-deoxy-3-S-(2,4-dinitrophenyl)-4-O-p-methoxybenzyl-3-thio-β-D-galactopyranose

There total 9 articles about 1,6-anhydro-2-azido-2-deoxy-3-S-(2,4-dinitrophenyl)-4-O-p-methoxybenzyl-3-thio-β-D-galactopyranose 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: 65.0%

2,4-Dinitrofluorobenzene (70-34-8,65727-75-5) + 1,6:2,3-dianhydro-2,3-epithio-4-O-p-methoxybenzyl-β-D-talopyranose (331633-94-4) → 1,6-anhydro-3-azido-3-deoxy-2-S-(2,4-dinitrophenyl)-4-O-p-methoxybenzyl-2-thio-β-D-idopyranose + 1,6-anhydro-2-azido-2-deoxy-3-S-(2,4-dinitrophenyl)-4-O-p-methoxybenzyl-3-thio-β-D-galactopyranose (331633-97-7)

Guidance literature:

1,6:2,3-dianhydro-2,3-epithio-4-O-p-methoxybenzyl-β-D-talopyranose; With mercury(II) diacetate; tetrabutylammoniun azide; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 24h;

2,4-Dinitrofluorobenzene; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 18h; Further stages.;

DOI:10.1021/ja003713q

Reference yield:

1,6-anhydro-2,3-dideoxy-β-threo-hex-2-enopyranose (58394-32-4,52630-80-5,52630-81-6) → 1,6-anhydro-2-azido-2-deoxy-3-S-(2,4-dinitrophenyl)-4-O-p-methoxybenzyl-3-thio-β-D-galactopyranose (331633-97-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: NaH; TBAI / dimethylformamide / 0.17 h / 0 °C

1.2: 62 percent / dimethylformamide / 12 h / 20 °C

2.1: 90 percent / aq. OsO₄; NMO / acetone; 2-methyl-propan-2-ol / 3 h / 0 °C

3.1: SOCl₂; Et₃N / CH₂Cl₂ / 0 °C

3.2: 66 percent / aq.NaIO₄; RuCl₃ / CCl₄; acetonitrile / 0.25 h / 20 °C

4.1: KSAc / dimethylformamide / 2 h / 60 °C

4.2: 91 percent / NaOMe / methanol / 0.5 h / 20 °C

5.1: TBAN₃; Hg(OAc)2 / dimethylformamide / 24 h / 0 - 20 °C

5.2: 65 percent / DIEA / CH₂Cl₂ / 18 h / 20 °C

With osmium(VIII) oxide; thionyl chloride; N-methyl-2-indolinone; mercury(II) diacetate; tetrabutylammoniun azide; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; potassium thioacetate; In dichloromethane; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;

DOI:10.1021/ja003713q

Reference yield:

1,6-anhydro-2,3-dideoxy-β-D-erythro-hex-2-enopyranose (58394-31-3,52630-80-5,52630-81-6) → 1,6-anhydro-2-azido-2-deoxy-3-S-(2,4-dinitrophenyl)-4-O-p-methoxybenzyl-3-thio-β-D-galactopyranose (331633-97-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: NMO; TPAP; 4A molecular sieves / CH₂Cl₂ / 1 h / 20 °C

2.1: CeCl₃; NaBH₄ / CH₂Cl₂; methanol / 1 h / -78 °C

3.1: NaH; TBAI / dimethylformamide / 0.17 h / 0 °C

3.2: 62 percent / dimethylformamide / 12 h / 20 °C

4.1: 90 percent / aq. OsO₄; NMO / acetone; 2-methyl-propan-2-ol / 3 h / 0 °C

5.1: SOCl₂; Et₃N / CH₂Cl₂ / 0 °C

5.2: 66 percent / aq.NaIO₄; RuCl₃ / CCl₄; acetonitrile / 0.25 h / 20 °C

6.1: KSAc / dimethylformamide / 2 h / 60 °C

6.2: 91 percent / NaOMe / methanol / 0.5 h / 20 °C

7.1: TBAN₃; Hg(OAc)2 / dimethylformamide / 24 h / 0 - 20 °C

7.2: 65 percent / DIEA / CH₂Cl₂ / 18 h / 20 °C

With sodium tetrahydroborate; osmium(VIII) oxide; thionyl chloride; N-methyl-2-indolinone; cerium(III) chloride; tetrapropylammonium perruthennate; 4 A molecular sieve; mercury(II) diacetate; tetrabutylammoniun azide; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; potassium thioacetate; In methanol; dichloromethane; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;

DOI:10.1021/ja003713q

upstream raw materials:

2,4-Dinitrofluorobenzene

1,6:2,3-dianhydro-2,3-epithio-4-O-p-methoxybenzyl-β-D-talopyranose

1,6-anhydro-2,3-dideoxy-β-threo-hex-2-enopyranose

1,6-anhydro-2,3-dideoxy-β-D-erythro-hex-2-enopyranose