(4R,5S)-3-[(2R,3S,4S,5S,6S,7R)-6-(tert-Butyl-dimethyl-silanyloxy)-4-((Z)-3-iodo-2-methyl-allyl)-8-(4-methoxy-benzyloxy)-2,5,7-trimethyl-3-triethylsilanyloxy-octanoyl]-4-methyl-5-phenyl-oxazolidin-2-one

Base Information

• Chemical Name: (4R,5S)-3-[(2R,3S,4S,5S,6S,7R)-6-(tert-Butyl-dimethyl-silanyloxy)-4-((Z)-3-iodo-2-methyl-allyl)-8-(4-methoxy-benzyloxy)-2,5,7-trimethyl-3-triethylsilanyloxy-octanoyl]-4-methyl-5-phenyl-oxazolidin-2-one
• CAS No.: 412342-82-6
• Molecular Formula: C₄₅H₇₂INO₇Si₂
• Molecular Weight: 922.145
• Mol file: 412342-82-6.mol

Synonyms:(4R,5S)-3-[(2R,3S,4S,5S,6S,7R)-6-(tert-Butyl-dimethyl-silanyloxy)-4-((Z)-3-iodo-2-methyl-allyl)-8-(4-methoxy-benzyloxy)-2,5,7-trimethyl-3-triethylsilanyloxy-octanoyl]-4-methyl-5-phenyl-oxazolidin-2-one

Chemical Property of (4R,5S)-3-[(2R,3S,4S,5S,6S,7R)-6-(tert-Butyl-dimethyl-silanyloxy)-4-((Z)-3-iodo-2-methyl-allyl)-8-(4-methoxy-benzyloxy)-2,5,7-trimethyl-3-triethylsilanyloxy-octanoyl]-4-methyl-5-phenyl-oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5S)-3-[(2R,3S,4S,5S,6S,7R)-6-(tert-Butyl-dimethyl-silanyloxy)-4-((Z)-3-iodo-2-methyl-allyl)-8-(4-methoxy-benzyloxy)-2,5,7-trimethyl-3-triethylsilanyloxy-octanoyl]-4-methyl-5-phenyl-oxazolidin-2-one

There total 14 articles about (4R,5S)-3-[(2R,3S,4S,5S,6S,7R)-6-(tert-Butyl-dimethyl-silanyloxy)-4-((Z)-3-iodo-2-methyl-allyl)-8-(4-methoxy-benzyloxy)-2,5,7-trimethyl-3-triethylsilanyloxy-octanoyl]-4-methyl-5-phenyl-oxazolidin-2-one 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:

(2R,3S,4S)-1-(tert-Butyl-diphenyl-silanyloxy)-2,4-dimethyl-hex-5-en-3-ol → (4R,5S)-3-[(2R,3S,4S,5S,6S,7R)-6-(tert-Butyl-dimethyl-silanyloxy)-4-((Z)-3-iodo-2-methyl-allyl)-8-(4-methoxy-benzyloxy)-2,5,7-trimethyl-3-triethylsilanyloxy-octanoyl]-4-methyl-5-phenyl-oxazolidin-2-one (412342-82-6)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 92 percent / TfOH / CH₂Cl₂ / 3.5 h / 20 °C

2.1: catecholborane / (Ph₃P)3RhCl / tetrahydrofuran / 0 - 20 °C

2.2: 27.5percent H₂O₂; 2N NaOH / methanol / 2 h / 0 °C

3.1: PDC / dimethylformamide / 48 h / 20 °C

4.1: 73 percent / H₂ / 20percent Pd(OH)2/C / methanol

5.1: Li(Pr-i)2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / -78 °C

5.2: 86 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / -78 °C

6.1: aq. HF / tetrahydrofuran; acetonitrile / 20 °C

7.1: PPTS / CH₂Cl₂ / 7 h / 20 °C

8.1: LiBH₄ / tetrahydrofuran; methanol / 3 h / Heating

9.1: imidazole / dimethylformamide / 1.5 h / 0 °C

10.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -50 °C

11.1: aq. HF / tetrahydrofuran; acetonitrile / 1.5 h / 20 °C

12.1: TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.67 h / 20 °C

13.1: (n-Bu)2BOTf; Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

13.2: CH₂Cl₂ / -78 - 20 °C

14.1: 2,6-lutidine / CH₂Cl₂ / 0.75 h / -50 - 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; dipyridinium dichromate; lithium borohydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; trifluorormethanesulfonic acid; 4 A molecular sieve; Li(Pr-i)2; di-n-butylboryl trifluoromethanesulfonate; hydrogen fluoride; hydrogen; pyridinium p-toluenesulfonate; triethylamine; benzo[1,3,2]dioxaborole; Wilkinson's catalyst; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 13.2: Evans aldol addition;

DOI:10.1021/ol017266a

Reference yield:

((2R,3S,4S)-3-Benzyloxy-2,4-dimethyl-hex-5-enyloxy)-tert-butyl-diphenyl-silane (412342-77-9) → (4R,5S)-3-[(2R,3S,4S,5S,6S,7R)-6-(tert-Butyl-dimethyl-silanyloxy)-4-((Z)-3-iodo-2-methyl-allyl)-8-(4-methoxy-benzyloxy)-2,5,7-trimethyl-3-triethylsilanyloxy-octanoyl]-4-methyl-5-phenyl-oxazolidin-2-one (412342-82-6)

Guidance literature:

Multi-step reaction with 13 steps

1.1: catecholborane / (Ph₃P)3RhCl / tetrahydrofuran / 0 - 20 °C

1.2: 27.5percent H₂O₂; 2N NaOH / methanol / 2 h / 0 °C

2.1: PDC / dimethylformamide / 48 h / 20 °C

3.1: 73 percent / H₂ / 20percent Pd(OH)2/C / methanol

4.1: Li(Pr-i)2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / -78 °C

4.2: 86 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / -78 °C

5.1: aq. HF / tetrahydrofuran; acetonitrile / 20 °C

6.1: PPTS / CH₂Cl₂ / 7 h / 20 °C

7.1: LiBH₄ / tetrahydrofuran; methanol / 3 h / Heating

8.1: imidazole / dimethylformamide / 1.5 h / 0 °C

9.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -50 °C

10.1: aq. HF / tetrahydrofuran; acetonitrile / 1.5 h / 20 °C

11.1: TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.67 h / 20 °C

12.1: (n-Bu)2BOTf; Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

12.2: CH₂Cl₂ / -78 - 20 °C

13.1: 2,6-lutidine / CH₂Cl₂ / 0.75 h / -50 - 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; dipyridinium dichromate; lithium borohydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; Li(Pr-i)2; di-n-butylboryl trifluoromethanesulfonate; hydrogen fluoride; hydrogen; pyridinium p-toluenesulfonate; triethylamine; benzo[1,3,2]dioxaborole; Wilkinson's catalyst; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 12.2: Evans aldol addition;

DOI:10.1021/ol017266a

Reference yield:

(3S,4S,5R)-4-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hexan-1-ol → (4R,5S)-3-[(2R,3S,4S,5S,6S,7R)-6-(tert-Butyl-dimethyl-silanyloxy)-4-((Z)-3-iodo-2-methyl-allyl)-8-(4-methoxy-benzyloxy)-2,5,7-trimethyl-3-triethylsilanyloxy-octanoyl]-4-methyl-5-phenyl-oxazolidin-2-one (412342-82-6)

Guidance literature:

Multi-step reaction with 12 steps

1.1: PDC / dimethylformamide / 48 h / 20 °C

2.1: 73 percent / H₂ / 20percent Pd(OH)2/C / methanol

3.1: Li(Pr-i)2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / -78 °C

3.2: 86 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / -78 °C

4.1: aq. HF / tetrahydrofuran; acetonitrile / 20 °C

5.1: PPTS / CH₂Cl₂ / 7 h / 20 °C

6.1: LiBH₄ / tetrahydrofuran; methanol / 3 h / Heating

7.1: imidazole / dimethylformamide / 1.5 h / 0 °C

8.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -50 °C

9.1: aq. HF / tetrahydrofuran; acetonitrile / 1.5 h / 20 °C

10.1: TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.67 h / 20 °C

11.1: (n-Bu)2BOTf; Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

11.2: CH₂Cl₂ / -78 - 20 °C

12.1: 2,6-lutidine / CH₂Cl₂ / 0.75 h / -50 - 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; dipyridinium dichromate; lithium borohydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; Li(Pr-i)2; di-n-butylboryl trifluoromethanesulfonate; hydrogen fluoride; hydrogen; pyridinium p-toluenesulfonate; triethylamine; 20percent Pd(OH)2/C; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 11.2: Evans aldol addition;

DOI:10.1021/ol017266a

upstream raw materials:

triethylsilyl trifluoromethyl sulfonate

(4R,5S)-3-[(2R,3S,4S,5S,6S,7R)-6-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-4-((Z)-3-iodo-2-methyl-allyl)-8-(4-methoxy-benzyloxy)-2,5,7-trimethyl-octanoyl]-4-methyl-5-phenyl-oxazolidin-2-one

(4S,5S)-5-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-4-methyl-dihydro-furan-2-one

(3S,4S,5S)-3-((Z)-3-Iodo-2-methyl-allyl)-5-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-4-methyl-dihydro-furan-2-one

Downstream raw materials:

(2E,4E)-(6S,7R,8S,9S,10S,11R)-10-(tert-Butyl-dimethyl-silanyloxy)-8-((Z)-3-iodo-2-methyl-allyl)-12-(4-methoxy-benzyloxy)-2,4,6,9,11-pentamethyl-7-triethylsilanyloxy-dodeca-2,4-dienoic acid ethyl ester

(E)-(4S,5R,6S,7S,8S,9R)-8-(tert-Butyl-dimethyl-silanyloxy)-6-((Z)-3-iodo-2-methyl-allyl)-10-(4-methoxy-benzyloxy)-2,4,7,9-tetramethyl-5-triethylsilanyloxy-dec-2-enoic acid ethyl ester

(E)-(4S,5R,6S,7S,8S,9R)-8-(tert-Butyl-dimethyl-silanyloxy)-6-((Z)-3-iodo-2-methyl-allyl)-10-(4-methoxy-benzyloxy)-2,4,7,9-tetramethyl-5-triethylsilanyloxy-dec-2-en-1-ol

(E)-(4S,5R,6S,7S,8S,9R)-8-(tert-Butyl-dimethyl-silanyloxy)-6-((Z)-3-iodo-2-methyl-allyl)-10-(4-methoxy-benzyloxy)-2,4,7,9-tetramethyl-5-triethylsilanyloxy-dec-2-enal