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

Base Information

• Chemical Name: 4,6,8-trideoxy-4,6-di-C-methyl-5-O-(p-methoxybenzyl)-7-O-(tert-butyldimethylsilyl)-D-threo-L-galactoctanoic acid ethyl ester
• CAS No.: 135589-35-4
• Molecular Formula: C₂₆H₄₆O₇Si
• Molecular Weight: 498.733
• Mol file: 135589-35-4.mol

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

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

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-galactoctanoic acid ethyl ester

There total 12 articles about 4,6,8-trideoxy-4,6-di-C-methyl-5-O-(p-methoxybenzyl)-7-O-(tert-butyldimethylsilyl)-D-threo-L-galactoctanoic acid ethyl ester 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: 68.0%

2,4,6-trideoxy-2,4-di-C-methyl-carbethoxymethylidene-3-O-(p-methoxybenzyl)-5-O-(tert-butyldimethylsilyl)-D-galactose (135589-32-1) → 4,6,8-trideoxy-4,6-di-C-methyl-5-O-(p-methoxybenzyl)-7-O-(tert-butyldimethylsilyl)-D-threo-L-idooctanoic acid ethyl ester (135589-33-2) + 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)

Guidance literature:

With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; acetone; at 20 ℃; for 2h;

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-galactoctanoic acid ethyl ester (135589-35-4)

Guidance literature:

Multi-step reaction with 11 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

With pyridine; sodium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; oxalyl dichloride; potassium tert-butylate; mercury(II) diacetate; pyridinium p-toluenesulfonate; nickel; sodium hydride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; methanol; 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-galactoctanoic acid ethyl ester (135589-35-4)

Guidance literature:

Multi-step reaction with 5 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

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

DOI:10.1007/BF00960425

upstream raw materials:

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

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

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