(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

Base Information

• Chemical Name: (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
• CAS No.: 212508-16-2
• Molecular Formula: C₄₃H₆₉NO₆SSi
• Molecular Weight: 756.175
• Mol file: 212508-16-2.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 20 articles about (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 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:

(E)-5-(benzyloxy)-4,4-dimethylpent-2-en-1-ol (121352-87-2) → (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 (212508-16-2)

Guidance literature:

Multi-step reaction with 20 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

8: TBAF / tetrahydrofuran / 0.5 h

9: TsOH / 0.25 h

10: 1.) catecholborane, 2.) H₂O₂, NaOH / 1.) (PPh₃)3RhCl / 1.) THF, 45 min

11: 1.) (COCl)2, DMSO, 2.) Et₃N

12: NaH / tetrahydrofuran / 4 h

13: H₂ / 10percent Pd/C / ethanol; ethyl acetate / 5 h

14: tetrahydrofuran / 3 h

15: HCl, H₂O / tetrahydrofuran / 3 h / 50 °C

16: 90 percent / TsOH / benzene / 0.5 h

17: 94 percent / 2,6-lutidine / CH₂Cl₂ / 4 h / -78 °C

18: 75 percent / DIBAL-H / CH₂Cl₂ / 1.5 h / -78 - -15 °C

19: 1.) (COCl)2, DMSO, 2.) Et₃N

With 2,6-dimethylpyridine; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; sodium hydroxide; oxalyl dichloride; diethyl (2R,3R)-tartrate; L-(+)-diisopropyl tartrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; water; hydrogen; dihydrogen peroxide; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; benzo[1,3,2]dioxaborole; palladium on activated charcoal; Wilkinson's catalyst; In tetrahydrofuran; ethanol; hexane; dichloromethane; ethyl acetate; 1,2-dichloro-ethane; toluene; benzene;

DOI:10.1039/a802947d

Reference yield:

((2S,3S)-3-(1-(benzyloxy)-2-methylpropan-2-yl)oxiran-2-yl)methanol (130199-57-4) → (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 (212508-16-2)

Guidance literature:

Multi-step reaction with 19 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

7: TBAF / tetrahydrofuran / 0.5 h

8: TsOH / 0.25 h

9: 1.) catecholborane, 2.) H₂O₂, NaOH / 1.) (PPh₃)3RhCl / 1.) THF, 45 min

10: 1.) (COCl)2, DMSO, 2.) Et₃N

11: NaH / tetrahydrofuran / 4 h

12: H₂ / 10percent Pd/C / ethanol; ethyl acetate / 5 h

13: tetrahydrofuran / 3 h

14: HCl, H₂O / tetrahydrofuran / 3 h / 50 °C

15: 90 percent / TsOH / benzene / 0.5 h

16: 94 percent / 2,6-lutidine / CH₂Cl₂ / 4 h / -78 °C

17: 75 percent / DIBAL-H / CH₂Cl₂ / 1.5 h / -78 - -15 °C

18: 1.) (COCl)2, DMSO, 2.) Et₃N

With 2,6-dimethylpyridine; hydrogenchloride; sodium hydroxide; oxalyl dichloride; L-(+)-diisopropyl tartrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; water; hydrogen; dihydrogen peroxide; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; benzo[1,3,2]dioxaborole; palladium on activated charcoal; Wilkinson's catalyst; In tetrahydrofuran; ethanol; hexane; dichloromethane; ethyl acetate; 1,2-dichloro-ethane; toluene; benzene;

DOI:10.1039/a802947d

Reference yield:

(2R,3S)-3-(2-Benzyloxy-1,1-dimethyl-ethyl)-oxirane-2-carbaldehyde → (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 (212508-16-2)

Guidance literature:

Multi-step reaction with 18 steps

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

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

3: 2,6-lutidine / CH₂Cl₂ / 0.75 h

5: 93 percent / (R,R)-diisopropyl tartrate, 4 Angstroem molecular sieves / toluene / 1.) -78 deg C, 3 h, 2.) r.t., 12 h

6: TBAF / tetrahydrofuran / 0.5 h

7: TsOH / 0.25 h

8: 1.) catecholborane, 2.) H₂O₂, NaOH / 1.) (PPh₃)3RhCl / 1.) THF, 45 min

9: 1.) (COCl)2, DMSO, 2.) Et₃N

10: NaH / tetrahydrofuran / 4 h

11: H₂ / 10percent Pd/C / ethanol; ethyl acetate / 5 h

12: tetrahydrofuran / 3 h

13: HCl, H₂O / tetrahydrofuran / 3 h / 50 °C

14: 90 percent / TsOH / benzene / 0.5 h

15: 94 percent / 2,6-lutidine / CH₂Cl₂ / 4 h / -78 °C

16: 75 percent / DIBAL-H / CH₂Cl₂ / 1.5 h / -78 - -15 °C

17: 1.) (COCl)2, DMSO, 2.) Et₃N

With 2,6-dimethylpyridine; hydrogenchloride; sodium hydroxide; oxalyl dichloride; L-(+)-diisopropyl tartrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; water; hydrogen; dihydrogen peroxide; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; benzo[1,3,2]dioxaborole; palladium on activated charcoal; Wilkinson's catalyst; In tetrahydrofuran; ethanol; hexane; dichloromethane; ethyl acetate; 1,2-dichloro-ethane; toluene; benzene;

DOI:10.1039/a802947d

upstream raw materials:

(1S)-[(1E)-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethynyl]-3-butenyl acetate

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

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

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

Downstream raw materials:

epothilone D

(4S,7R,8S,9S,13Z,16S,1'E)-4,8-di-tert-butyldimethylsilyloxy-5,5,7,9,13-pentamethyl-16-[1-methyl-2-(2-methyl-1,3-thiazol-4-yl)-1-ethenyl]-1-oxa-13-cyclohexadecene-2,6-dione

epothilone B