(3S,4S,5R,6R)-8-Benzyloxy-3,5,7,7-tetramethyl-6-triethylsilanyloxy-oct-1-en-4-ol

Base Information

• Chemical Name: (3S,4S,5R,6R)-8-Benzyloxy-3,5,7,7-tetramethyl-6-triethylsilanyloxy-oct-1-en-4-ol
• CAS No.: 856170-49-5
• Molecular Formula: C₂₅H₄₄O₃Si
• Molecular Weight: 420.708
• Mol file: 856170-49-5.mol

Synonyms:(3S,4S,5R,6R)-8-Benzyloxy-3,5,7,7-tetramethyl-6-triethylsilanyloxy-oct-1-en-4-ol

Chemical Property of (3S,4S,5R,6R)-8-Benzyloxy-3,5,7,7-tetramethyl-6-triethylsilanyloxy-oct-1-en-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S,5R,6R)-8-Benzyloxy-3,5,7,7-tetramethyl-6-triethylsilanyloxy-oct-1-en-4-ol

There total 7 articles about (3S,4S,5R,6R)-8-Benzyloxy-3,5,7,7-tetramethyl-6-triethylsilanyloxy-oct-1-en-4-ol 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: 93.0%

(E)-crotylboronate + (2S,3R)-5-Benzyloxy-2,4,4-trimethyl-3-triethylsilanyloxy-pentanal (212509-18-7) → (3S,4S,5R,6R)-8-Benzyloxy-3,5,7,7-tetramethyl-6-triethylsilanyloxy-oct-1-en-4-ol (856170-49-5)

Guidance literature:

With L-(+)-diisopropyl tartrate; 4 A molecular sieve; In toluene; 1.) -78 deg C, 3 h, 2.) r.t., 12 h;

DOI:10.1039/a802947d

Reference yield:

((2S,3S)-3-(1-(benzyloxy)-2-methylpropan-2-yl)oxiran-2-yl)methanol (130199-57-4) → (3S,4S,5R,6R)-8-Benzyloxy-3,5,7,7-tetramethyl-6-triethylsilanyloxy-oct-1-en-4-ol (856170-49-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) CH₂Cl₂, 0 deg C, 1 h

2: NaH / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) 0 deg C, 30 min

3: 87 percent / H₂O / hexane; 1,2-dichloro-ethane / -30 °C

4: 2,6-lutidine / CH₂Cl₂ / 0.75 h

6: 93 percent / (R,R)-diisopropyl tartrate, 4 Angstroem molecular sieves / toluene / 1.) -78 deg C, 3 h, 2.) r.t., 12 h

With 2,6-dimethylpyridine; oxalyl dichloride; L-(+)-diisopropyl tartrate; 4 A molecular sieve; water; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; 1,2-dichloro-ethane; toluene;

DOI:10.1039/a802947d

Reference yield:

(E)-5-(benzyloxy)-4,4-dimethylpent-2-en-1-ol (121352-87-2) → (3S,4S,5R,6R)-8-Benzyloxy-3,5,7,7-tetramethyl-6-triethylsilanyloxy-oct-1-en-4-ol (856170-49-5)

Guidance literature:

Multi-step reaction with 7 steps

1: diethyl L-tartrate, Ti(O-i-Pr)4, t-BuOOH, 4 Angstroem molecular sieves / CH₂Cl₂ / 1.) -40 deg C, 8 h, 2.) -10 deg C, 8 h

2: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) CH₂Cl₂, 0 deg C, 1 h

3: NaH / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) 0 deg C, 30 min

4: 87 percent / H₂O / hexane; 1,2-dichloro-ethane / -30 °C

5: 2,6-lutidine / CH₂Cl₂ / 0.75 h

7: 93 percent / (R,R)-diisopropyl tartrate, 4 Angstroem molecular sieves / toluene / 1.) -78 deg C, 3 h, 2.) r.t., 12 h

With 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; oxalyl dichloride; diethyl (2R,3R)-tartrate; L-(+)-diisopropyl tartrate; 4 A molecular sieve; water; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; 1,2-dichloro-ethane; toluene;

DOI:10.1039/a802947d

upstream raw materials:

(2S,3R)-5-Benzyloxy-2,4,4-trimethyl-3-triethylsilanyloxy-pentanal

(E)-5-(benzyloxy)-4,4-dimethylpent-2-en-1-ol

((2S,3S)-3-(1-(benzyloxy)-2-methylpropan-2-yl)oxiran-2-yl)methanol

(E)-3-[(2S,3S)-3-(2-Benzyloxy-1,1-dimethyl-ethyl)-oxiranyl]-acrylic acid ethyl ester

Downstream raw materials:

(3S,5R,6S,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-5-(4-methoxy-benzyloxy)-4,4,6,8,12-pentamethyl-tridec-12-enoic acid (S)-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-but-3-enyl ester

(3R,4S,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,2,4,6,10-pentamethyl-undec-10-enal

(3R,4S,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,2,4,6,10-pentamethyl-undec-10-en-1-ol

epothilone D