3,5,7-trideoxy-3,5-di-C-methyl-4-O-(p-methoxybenzyl)-6-O-(tert-butyldimethylsilyl)-1-isopropylidene-L-glucose

Base Information

• Chemical Name: 3,5,7-trideoxy-3,5-di-C-methyl-4-O-(p-methoxybenzyl)-6-O-(tert-butyldimethylsilyl)-1-isopropylidene-L-glucose
• CAS No.: 137818-44-1
• Molecular Formula: C₂₆H₄₆O₄Si
• Molecular Weight: 450.734
• Mol file: 137818-44-1.mol

Synonyms:3,5,7-trideoxy-3,5-di-C-methyl-4-O-(p-methoxybenzyl)-6-O-(tert-butyldimethylsilyl)-1-isopropylidene-L-glucose

Chemical Property of 3,5,7-trideoxy-3,5-di-C-methyl-4-O-(p-methoxybenzyl)-6-O-(tert-butyldimethylsilyl)-1-isopropylidene-L-glucose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,5,7-trideoxy-3,5-di-C-methyl-4-O-(p-methoxybenzyl)-6-O-(tert-butyldimethylsilyl)-1-isopropylidene-L-glucose

There total 13 articles about 3,5,7-trideoxy-3,5-di-C-methyl-4-O-(p-methoxybenzyl)-6-O-(tert-butyldimethylsilyl)-1-isopropylidene-L-glucose 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:

(3R,4S,5S,6R)-4-Benzyloxy-2-methoxy-3,5,6-trimethyl-tetrahydro-pyran (81076-93-9,101628-76-6,135681-50-4) → 3,5,7-trideoxy-3,5-di-C-methyl-4-O-(p-methoxybenzyl)-6-O-(tert-butyldimethylsilyl)-1-isopropylidene-L-glucose (137818-44-1)

Guidance literature:

Multi-step reaction with 10 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

6: 93 percent / pyridine / 1 h / -35 °C

7: 100 percent / triethylamine / CH₂Cl₂ / 0.17 h / -25 °C

8: 92 percent / 15percent aq. NaOH / ethanol / 0.5 h / Heating

9: 100 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 0.5 h / -60 °C

10: 1.) t-BuLi, copper (I) bromide, dimethylsulfide

With pyridine; sodium hydroxide; sodium tetrahydroborate; oxalyl dichloride; dimethylsulfide; potassium tert-butylate; mercury(II) diacetate; tert.-butyl lithium; pyridinium p-toluenesulfonate; nickel; sodium hydride; dimethyl sulfoxide; triethylamine; copper(I) bromide; In methanol; ethanol; dichloromethane;

DOI:10.1007/BF00960425

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → 3,5,7-trideoxy-3,5-di-C-methyl-4-O-(p-methoxybenzyl)-6-O-(tert-butyldimethylsilyl)-1-isopropylidene-L-glucose (137818-44-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / triethylamine / CH₂Cl₂ / 0.17 h / -25 °C

2: 92 percent / 15percent aq. NaOH / ethanol / 0.5 h / Heating

3: 100 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 0.5 h / -60 °C

4: 1.) t-BuLi, copper (I) bromide, dimethylsulfide

With sodium hydroxide; oxalyl dichloride; dimethylsulfide; tert.-butyl lithium; dimethyl sulfoxide; triethylamine; copper(I) bromide; In ethanol; dichloromethane;

DOI:10.1007/BF00960425

Reference yield:

allyl-α,β-2,4,6-trideoxy-2,4-di-C-methyl-3-hydroxy-D-galactopyranoside (135589-24-1,135681-52-6) → 3,5,7-trideoxy-3,5-di-C-methyl-4-O-(p-methoxybenzyl)-6-O-(tert-butyldimethylsilyl)-1-isopropylidene-L-glucose (137818-44-1)

Guidance literature:

Multi-step reaction with 8 steps

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

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

3: 70.5 percent / NaBH₄ / ethanol

4: 93 percent / pyridine / 1 h / -35 °C

5: 100 percent / triethylamine / CH₂Cl₂ / 0.17 h / -25 °C

6: 92 percent / 15percent aq. NaOH / ethanol / 0.5 h / Heating

7: 100 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 0.5 h / -60 °C

8: 1.) t-BuLi, copper (I) bromide, dimethylsulfide

With pyridine; sodium hydroxide; sodium tetrahydroborate; oxalyl dichloride; dimethylsulfide; potassium tert-butylate; mercury(II) diacetate; tert.-butyl lithium; sodium hydride; dimethyl sulfoxide; triethylamine; copper(I) bromide; In ethanol; dichloromethane;

DOI:10.1007/BF00960425

upstream raw materials:

2-methyl-1-propenylbromide

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

t-butyldimethylsiyl triflate

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