methyl 2,4,6-trideoxy-2,4-di-C-methylgluohexopyranoside

Base Information

• Chemical Name: methyl 2,4,6-trideoxy-2,4-di-C-methylgluohexopyranoside
• CAS No.: 119816-53-4
• Molecular Formula: C₉H₁₈O₃
• Molecular Weight: 174.24
• Mol file: 119816-53-4.mol

Synonyms:methyl 2,4,6-trideoxy-2,4-di-C-methylgluohexopyranoside

Chemical Property of methyl 2,4,6-trideoxy-2,4-di-C-methylgluohexopyranoside

Chemical Property:

• Vapor Pressure: 0.00301mmHg at 25°C
• Boiling Point: 252.4°Cat760mmHg
• Flash Point: 106.5°C
• PSA: 38.69000
• Density: 1.01g/cm³
• LogP: 1.01070

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of methyl 2,4,6-trideoxy-2,4-di-C-methylgluohexopyranoside

There total 1 articles about methyl 2,4,6-trideoxy-2,4-di-C-methylgluohexopyranoside 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: 92.0%

(3R,4S,5S,6R)-4-Benzyloxy-2-methoxy-3,5,6-trimethyl-tetrahydro-pyran (81076-93-9,101628-76-6,135681-50-4) → 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)

Guidance literature:

With nickel; In methanol; for 2h; Heating;

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

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)-5-O-(tert-butyldimethylsilyl)-D-dulcite (135589-30-9)

Guidance literature:

Multi-step reaction with 7 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

5: 93 percent / pyridine / 1 h / -35 °C

6: 100 percent / triethylamine / CH₂Cl₂ / 0.17 h / -25 °C

7: 92 percent / 15percent aq. NaOH / ethanol / 0.5 h / Heating

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

DOI:10.1007/BF00960425

upstream raw materials:

(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)-D-dulcite

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

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

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

Refernces