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

Base Information

Chemical Name:4,6,8-trideoxy-4,6-di-C-methyl-5-O-(4-methoxybenzylidene)-7-O-(tert-butyldimethylsilyl)-D-threo-L-galactooctanol
CAS No.:135589-37-6
Molecular Formula:C₂₄H₄₂O₆Si
Molecular Weight:454.679
Hs Code.:

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

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

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

There total 14 articles about 4,6,8-trideoxy-4,6-di-C-methyl-5-O-(4-methoxybenzylidene)-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: 98.8%

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

: 135589-37-6
4,6,8-trideoxy-4,6-di-C-methyl-5-O-(4-methoxybenzylidene)-7-O-(tert-butyldimethylsilyl)-D-threo-L-galactooctanol

Guidance literature:: With 3 A molecular sieve; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; for 0.166667h;
DOI:10.1007/BF00960425

Reference yield:

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

: 135589-37-6
4,6,8-trideoxy-4,6-di-C-methyl-5-O-(4-methoxybenzylidene)-7-O-(tert-butyldimethylsilyl)-D-threo-L-galactooctanol

Guidance literature:: Multi-step reaction with 13 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

13: 98.8 percent / dichlorodicyanobenzoquinone (DDQ), 3A molecular sieves / CH₂Cl₂ / 0.17 h

With pyridine; sodium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; lithium aluminium tetrahydride; oxalyl dichloride; 3 A molecular sieve; potassium tert-butylate; mercury(II) diacetate; pyridinium p-toluenesulfonate; nickel; sodium hydride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; acetone;
DOI:10.1007/BF00960425

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 135589-37-6
4,6,8-trideoxy-4,6-di-C-methyl-5-O-(4-methoxybenzylidene)-7-O-(tert-butyldimethylsilyl)-D-threo-L-galactooctanol

Guidance literature:: Multi-step reaction with 7 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

7: 98.8 percent / dichlorodicyanobenzoquinone (DDQ), 3A molecular sieves / CH₂Cl₂ / 0.17 h

With sodium hydroxide; osmium(VIII) oxide; lithium aluminium tetrahydride; oxalyl dichloride; 3 A molecular sieve; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; acetone;
DOI:10.1007/BF00960425