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

Base Information

• Chemical Name: 4,6,8-trideoxy-4,6-di-C-methyl-5-O-(p-methoxybenzyl)-7-O-(tert-butyldimethylsilyl)-D-threo-L-galactooctanol
• CAS No.: 135589-36-5
• Molecular Formula: C₂₄H₄₄O₆Si
• Molecular Weight: 456.695
• Mol file: 135589-36-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 13 articles about 4,6,8-trideoxy-4,6-di-C-methyl-5-O-(p-methoxybenzyl)-7-O-(tert-butyldimethylsilyl)-D-threo-L-galactooctanol 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: 35.0%

4,6,8-trideoxy-4,6-di-C-methyl-5-O-(p-methoxybenzyl)-7-O-(tert-butyldimethylsilyl)-D-threo-L-galactoctanoic acid ethyl ester (135589-35-4) → 4,6,8-trideoxy-4,6-di-C-methyl-5-O-(p-methoxybenzyl)-7-O-(tert-butyldimethylsilyl)-D-threo-L-galactooctanol (135589-36-5)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at -30 - 10 ℃; for 1h;

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) → 4,6,8-trideoxy-4,6-di-C-methyl-5-O-(p-methoxybenzyl)-7-O-(tert-butyldimethylsilyl)-D-threo-L-galactooctanol (135589-36-5)

Guidance literature:

Multi-step reaction with 12 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: 78 percent / tetrahydrofuran / 2.5 h / Heating

11: 68 percent / N-methylmorpholine N-oxide, OsO₄ / acetone; H₂O / 2 h / 20 °C

12: 35 percent / LiAlH₄ / diethyl ether / 1 h / -30 - 10 °C

With pyridine; sodium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; lithium aluminium tetrahydride; oxalyl dichloride; potassium tert-butylate; mercury(II) diacetate; pyridinium p-toluenesulfonate; nickel; sodium hydride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; acetone;

DOI:10.1007/BF00960425

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → 4,6,8-trideoxy-4,6-di-C-methyl-5-O-(p-methoxybenzyl)-7-O-(tert-butyldimethylsilyl)-D-threo-L-galactooctanol (135589-36-5)

Guidance literature:

Multi-step reaction with 6 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: 78 percent / tetrahydrofuran / 2.5 h / Heating

5: 68 percent / N-methylmorpholine N-oxide, OsO₄ / acetone; H₂O / 2 h / 20 °C

6: 35 percent / LiAlH₄ / diethyl ether / 1 h / -30 - 10 °C

With sodium hydroxide; osmium(VIII) oxide; lithium aluminium tetrahydride; oxalyl dichloride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; acetone;

DOI:10.1007/BF00960425

upstream raw materials:

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

t-butyldimethylsiyl triflate

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

Downstream raw materials:

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

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