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

Base Information

• Chemical Name: 3,5,7-trideoxy-3,5-di-C-methyl-2,4-O-(4-methoxybenzylidene)-5-O-(tert-butyldimethylsilyl)-D-glycero-L-mannoheptitol
• CAS No.: 135589-23-0
• Molecular Formula: C₂₃H₃₈O₅Si
• Molecular Weight: 422.637
• Mol file: 135589-23-0.mol

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

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

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-2,4-O-(4-methoxybenzylidene)-5-O-(tert-butyldimethylsilyl)-D-glycero-L-mannoheptitol

There total 15 articles about 3,5,7-trideoxy-3,5-di-C-methyl-2,4-O-(4-methoxybenzylidene)-5-O-(tert-butyldimethylsilyl)-D-glycero-L-mannoheptitol 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: 51.0%

4,6,8-trideoxy-4,6-di-C-methyl-5-O-(4-methoxybenzylidene)-7-O-(tert-butyldimethylsilyl)-D-threo-L-galactooctanol (135589-37-6) → 3,5,7-trideoxy-3,5-di-C-methyl-2,4-O-(4-methoxybenzylidene)-5-O-(tert-butyldimethylsilyl)-D-glycero-L-mannoheptitol (135589-23-0)

Guidance literature:

With lead(IV) acetate; sodium acetate; In acetonitrile; at -20 ℃; for 0.25h;

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) → 3,5,7-trideoxy-3,5-di-C-methyl-2,4-O-(4-methoxybenzylidene)-5-O-(tert-butyldimethylsilyl)-D-glycero-L-mannoheptitol (135589-23-0)

Guidance literature:

Multi-step reaction with 14 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

14: 51 percent / NaOAc, Pb(OAc)4 / acetonitrile / 0.25 h / -20 °C

With pyridine; lead(IV) acetate; sodium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; lithium aluminium tetrahydride; oxalyl dichloride; 3 A molecular sieve; potassium tert-butylate; mercury(II) diacetate; sodium acetate; 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; acetonitrile;

DOI:10.1007/BF00960425

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → 3,5,7-trideoxy-3,5-di-C-methyl-2,4-O-(4-methoxybenzylidene)-5-O-(tert-butyldimethylsilyl)-D-glycero-L-mannoheptitol (135589-23-0)

Guidance literature:

Multi-step reaction with 8 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

8: 51 percent / NaOAc, Pb(OAc)4 / acetonitrile / 0.25 h / -20 °C

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

DOI:10.1007/BF00960425

upstream raw materials:

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

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