1,6-anhydro-2-desoxy-2-C-methyl-3-O-(4-methoxybenzyl)-β-D-xylo-hexapyranoz-4-ylose

Base Information

• Chemical Name: 1,6-anhydro-2-desoxy-2-C-methyl-3-O-(4-methoxybenzyl)-β-D-xylo-hexapyranoz-4-ylose
• CAS No.: 123493-65-2
• Molecular Formula: C₁₅H₁₈O₅
• Molecular Weight: 278.305
• Mol file: 123493-65-2.mol

Synonyms:1,6-anhydro-2-desoxy-2-C-methyl-3-O-(4-methoxybenzyl)-β-D-xylo-hexapyranoz-4-ylose

Chemical Property of 1,6-anhydro-2-desoxy-2-C-methyl-3-O-(4-methoxybenzyl)-β-D-xylo-hexapyranoz-4-ylose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,6-anhydro-2-desoxy-2-C-methyl-3-O-(4-methoxybenzyl)-β-D-xylo-hexapyranoz-4-ylose

There total 5 articles about 1,6-anhydro-2-desoxy-2-C-methyl-3-O-(4-methoxybenzyl)-β-D-xylo-hexapyranoz-4-ylose 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: 97.0%

1,6-anhydro-2-desoxy-2-C-methyl-3-O-(4-methoxybenzyl)-β-D-glucopyranose (123493-64-1) → 1,6-anhydro-2-desoxy-2-C-methyl-3-O-(4-methoxybenzyl)-β-D-xylo-hexapyranoz-4-ylose (123493-65-2)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -60 ℃; for 0.416667h;

DOI:10.1007/BF00958057

Reference yield:

4-O-allyl-1,6-anhydro-2-deoxy-2-C-methyl-β-D-glucopyranose (91510-64-4) → 1,6-anhydro-2-desoxy-2-C-methyl-3-O-(4-methoxybenzyl)-β-D-xylo-hexapyranoz-4-ylose (123493-65-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) NaH / 1) DMF, 1.5 h, 2) 2.5 h

2: 1) t-BuOK, 2) Hg(OAc)2 / 1) DMSO, 2 h, 2) acetone, H₂O, 10 min

3: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -60 deg C, 25 min, 2) -60 deg C up to 0 deg C, 3 min

With oxalyl dichloride; potassium tert-butylate; mercury(II) diacetate; sodium hydride; dimethyl sulfoxide; triethylamine;

DOI:10.1016/S0040-4020(01)96139-3

Reference yield:

1,6-anhydro-2-desoxy-2-C-methyl-4-O-allyl-3-O-(4-methoxybenzyl)-β-D-glucopyranose (123493-63-0) → 1,6-anhydro-2-desoxy-2-C-methyl-3-O-(4-methoxybenzyl)-β-D-xylo-hexapyranoz-4-ylose (123493-65-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) t-BuOK, 2) Hg(OAc)2 / 1) DMSO, 2 h, 2) acetone, H₂O, 10 min

2: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -60 deg C, 25 min, 2) -60 deg C up to 0 deg C, 3 min

With oxalyl dichloride; potassium tert-butylate; mercury(II) diacetate; dimethyl sulfoxide; triethylamine;

DOI:10.1016/S0040-4020(01)96139-3

upstream raw materials:

1,6-anhydro-2-desoxy-2-C-methyl-3-O-(4-methoxybenzyl)-β-D-glucopyranose

4-O-allyl-1,6-anhydro-2-deoxy-2-C-methyl-β-D-glucopyranose

1,6-anhydro-2-desoxy-2-C-methyl-4-O-allyl-3-O-(4-methoxybenzyl)-β-D-glucopyranose

4-O-Allyl-1,6:2,3-dianhydro-β-D-mannopyranose

Downstream raw materials:

1,6-anhydro-2,3-didesoxy-2,4-di-C-methyl-4-O-benzyl-β-D-galactopyranose

1,6-anhydro-2-desoxy-2,4-di-C-methyl-4-O-benzyl-β-D-galactopyranose

1,6-anhydro-2-desoxy-2,4-di-C-methyl-3-O-(4-methoxybenzyl)-4-O-benzyl-β-D-galactopyranose

Dithiocarbonic acid O-((1R,2R,3R,4R,5R)-2-benzyloxy-2,4-dimethyl-6,8-dioxa-bicyclo[3.2.1]oct-3-yl) ester S-methyl ester