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

Base Information

• Chemical Name: 1,6:2,3-dianhydro-2,3-epithio-4-O-p-methoxybenzyl-β-D-talopyranose
• CAS No.: 331633-94-4
• Molecular Formula: C₁₄H₁₆O₄S
• Molecular Weight: 280.345
• Mol file: 331633-94-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about 1,6:2,3-dianhydro-2,3-epithio-4-O-p-methoxybenzyl-β-D-talopyranose 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: 91.0%

1,6-anhydro-4-O-p-methoxybenzyl-β-D-gulopyranose 2,3-cyclic sulfate (331633-93-3) → 1,6:2,3-dianhydro-2,3-epithio-4-O-p-methoxybenzyl-β-D-talopyranose (331633-94-4)

Guidance literature:

1,6-anhydro-4-O-p-methoxybenzyl-β-D-gulopyranose 2,3-cyclic sulfate; With potassium thioacetate; In N,N-dimethyl-formamide; at 60 ℃; for 2h;

With sodium methylate; In methanol; at 20 ℃; for 0.5h; Further stages.;

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) → 1,6:2,3-dianhydro-2,3-epithio-4-O-p-methoxybenzyl-β-D-talopyranose (331633-94-4)

Guidance literature:

Multi-step reaction with 6 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

With sodium tetrahydroborate; osmium(VIII) oxide; thionyl chloride; N-methyl-2-indolinone; cerium(III) chloride; tetrapropylammonium perruthennate; 4 A molecular sieve; 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

Reference yield:

1,6-anhydro-2,3-dideoxy-β-threo-hex-2-enopyranose (58394-32-4,52630-80-5,52630-81-6) → 1,6:2,3-dianhydro-2,3-epithio-4-O-p-methoxybenzyl-β-D-talopyranose (331633-94-4)

Guidance literature:

Multi-step reaction with 4 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

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

DOI:10.1021/ja003713q

upstream raw materials:

1,6-anhydro-4-O-p-methoxybenzyl-β-D-gulopyranose 2,3-cyclic sulfate

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

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

isolevoglucosenone

Downstream raw materials:

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