2,4,6-trideoxy-2,4-di-C-methyl-3-O-(p-methoxybenzyl)-D-dulcite

Base Information

• Chemical Name: 2,4,6-trideoxy-2,4-di-C-methyl-3-O-(p-methoxybenzyl)-D-dulcite
• CAS No.: 135589-27-4
• Molecular Formula: C₁₆H₂₆O₄
• Molecular Weight: 282.38
• Mol file: 135589-27-4.mol

Synonyms:2,4,6-trideoxy-2,4-di-C-methyl-3-O-(p-methoxybenzyl)-D-dulcite

Chemical Property of 2,4,6-trideoxy-2,4-di-C-methyl-3-O-(p-methoxybenzyl)-D-dulcite

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,4,6-trideoxy-2,4-di-C-methyl-3-O-(p-methoxybenzyl)-D-dulcite

There total 5 articles about 2,4,6-trideoxy-2,4-di-C-methyl-3-O-(p-methoxybenzyl)-D-dulcite 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: 70.5%

2,4,6-trideoxy-2,4-di-C-methyl-3-O-p-methoxybenzyl-α,β-D-galactopyranose (135589-26-3,135681-54-8) → 2,4,6-trideoxy-2,4-di-C-methyl-3-O-(p-methoxybenzyl)-D-dulcite (135589-27-4)

Guidance literature:

With sodium tetrahydroborate; In ethanol;

DOI:10.1007/BF00960425

Reference yield:

(3R,4S,5S,6R)-4-Benzyloxy-2-methoxy-3,5,6-trimethyl-tetrahydro-pyran (81076-93-9,101628-76-6,135681-50-4) → 2,4,6-trideoxy-2,4-di-C-methyl-3-O-(p-methoxybenzyl)-D-dulcite (135589-27-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 92 percent / Raney nickel / methanol / 2 h / Heating

2: 81.2 percent / p-toluenesulfonic acid pyridinium salt (PPTS) / 4 h / Heating

3: 1.) NaH / 1.) DMF, 1 h, 2.) DMF, 12 h

4: 1.) t-BuOK, 2.) Hg(OAc)2 / 1.) DMSO, 100 deg C, 2 h, 2.) acetone, H₂O, 17 h

5: 70.5 percent / NaBH₄ / ethanol

With sodium tetrahydroborate; potassium tert-butylate; mercury(II) diacetate; pyridinium p-toluenesulfonate; nickel; sodium hydride; In methanol; ethanol;

DOI:10.1007/BF00960425

Reference yield:

methyl-α,β-2,4,6-trideoxy-2,4-di-C-methyl-D-galactopyranoside (3720-33-0,118397-46-9,118455-41-7,119816-53-4,119816-55-6,119816-56-7,129446-67-9,135681-51-5) → 2,4,6-trideoxy-2,4-di-C-methyl-3-O-(p-methoxybenzyl)-D-dulcite (135589-27-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 81.2 percent / p-toluenesulfonic acid pyridinium salt (PPTS) / 4 h / Heating

2: 1.) NaH / 1.) DMF, 1 h, 2.) DMF, 12 h

3: 1.) t-BuOK, 2.) Hg(OAc)2 / 1.) DMSO, 100 deg C, 2 h, 2.) acetone, H₂O, 17 h

4: 70.5 percent / NaBH₄ / ethanol

With sodium tetrahydroborate; potassium tert-butylate; mercury(II) diacetate; pyridinium p-toluenesulfonate; sodium hydride; In ethanol;

DOI:10.1007/BF00960425

upstream raw materials:

2,4,6-trideoxy-2,4-di-C-methyl-3-O-p-methoxybenzyl-α,β-D-galactopyranose

methyl-α,β-2,4,6-trideoxy-2,4-di-C-methyl-D-galactopyranoside

allyl-α,β-2,4,6-trideoxy-2,4-di-C-methyl-3-hydroxy-D-galactopyranoside

(3R,4S,5S,6R)-4-Benzyloxy-2-methoxy-3,5,6-trimethyl-tetrahydro-pyran

Downstream raw materials:

2,4,6-trideoxy-2,4-di-C-methyl-3-O-(p-methoxybenzyl)-5-O-(tert-butyldimethylsilyl)-D-dulcite

2,4,6-trideoxy-2,4-di-C-methyl-3-O-(p-methoxybenzyl)-5-O-(tert-butyldimethylsilyl)-D-galactose

3,5,7-trideoxy-3,5-di-C-methyl-2,4-O-(4-methoxybenzylidene)-5-O-(tert-butyldimethylsilyl)-D-glycero-L-mannoheptitol

4,6,8-trideoxy-4,6-di-C-methyl-5-O-(p-methoxybenzyl)-7-O-(tert-butyldimethylsilyl)-D-threo-L-galactooctanol