1,6-anhydro-4-O-p-methoxybenzyl-2,3-dideoxy-β-D-threo-hex-2-enopyranose

Base Information

• Chemical Name: 1,6-anhydro-4-O-p-methoxybenzyl-2,3-dideoxy-β-D-threo-hex-2-enopyranose
• CAS No.: 331633-91-1
• Molecular Formula: C₁₄H₁₆O₄
• Molecular Weight: 248.279
• Mol file: 331633-91-1.mol

Synonyms:1,6-anhydro-4-O-p-methoxybenzyl-2,3-dideoxy-β-D-threo-hex-2-enopyranose

Chemical Property of 1,6-anhydro-4-O-p-methoxybenzyl-2,3-dideoxy-β-D-threo-hex-2-enopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,6-anhydro-4-O-p-methoxybenzyl-2,3-dideoxy-β-D-threo-hex-2-enopyranose

There total 5 articles about 1,6-anhydro-4-O-p-methoxybenzyl-2,3-dideoxy-β-D-threo-hex-2-enopyranose 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: 62.0%

1,6-anhydro-2,3-dideoxy-β-threo-hex-2-enopyranose (58394-32-4,52630-80-5,52630-81-6) + p-methoxybenzyl chloride (824-94-2) → 1,6-anhydro-4-O-p-methoxybenzyl-2,3-dideoxy-β-D-threo-hex-2-enopyranose (331633-91-1)

Guidance literature:

1,6-anhydro-2,3-dideoxy-β-threo-hex-2-enopyranose; With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.166667h;

p-methoxybenzyl chloride; In N,N-dimethyl-formamide; at 20 ℃; for 12h; 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-anhydro-4-O-p-methoxybenzyl-2,3-dideoxy-β-D-threo-hex-2-enopyranose (331633-91-1)

Guidance literature:

Multi-step reaction with 3 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

With sodium tetrahydroborate; N-methyl-2-indolinone; cerium(III) chloride; tetrapropylammonium perruthennate; 4 A molecular sieve; tetra-(n-butyl)ammonium iodide; sodium hydride; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja003713q

Reference yield:

phenyl 4,6-di-O-acetyl-2,3-dideoxy-α/β-D-erythro-hex-2-enopyranoside (157905-00-5) → 1,6-anhydro-4-O-p-methoxybenzyl-2,3-dideoxy-β-D-threo-hex-2-enopyranose (331633-91-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: aq. NaOH / 3 h / Heating

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

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

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

4.2: 62 percent / dimethylformamide / 12 h / 20 °C

With sodium hydroxide; sodium tetrahydroborate; N-methyl-2-indolinone; cerium(III) chloride; tetrapropylammonium perruthennate; 4 A molecular sieve; tetra-(n-butyl)ammonium iodide; sodium hydride; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja003713q

upstream raw materials:

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

p-methoxybenzyl chloride

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

isolevoglucosenone

Downstream raw materials:

1,6-anhydro-4-O-p-methoxybenzyl-β-D-gulopyranose

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

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

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