11-(2,4-dimethyl-1-triethylsilanyloxy-hepta-2,5-dienyl)-10-hydroxy-16-methoxy-18-(4-methoxy-benzyloxy)-9,17,19,21,23-pentamethyl-20-triisopropylsilanyloxy-15-(2-trimethylsilanyl-ethoxymethoxy)-13-oxa-1,5-dithia-spiro[5.17]tricos-21-en-14-one

Base Information

• Chemical Name: 11-(2,4-dimethyl-1-triethylsilanyloxy-hepta-2,5-dienyl)-10-hydroxy-16-methoxy-18-(4-methoxy-benzyloxy)-9,17,19,21,23-pentamethyl-20-triisopropylsilanyloxy-15-(2-trimethylsilanyl-ethoxymethoxy)-13-oxa-1,5-dithia-spiro[5.17]tricos-21-en-14-one
• CAS No.: 777096-58-9
• Molecular Formula: C₆₄H₁₁₆O₁₀S₂Si₃
• Molecular Weight: 1194.01

Synonyms:11-(2,4-dimethyl-1-triethylsilanyloxy-hepta-2,5-dienyl)-10-hydroxy-16-methoxy-18-(4-methoxy-benzyloxy)-9,17,19,21,23-pentamethyl-20-triisopropylsilanyloxy-15-(2-trimethylsilanyl-ethoxymethoxy)-13-oxa-1,5-dithia-spiro[5.17]tricos-21-en-14-one

Chemical Property of 11-(2,4-dimethyl-1-triethylsilanyloxy-hepta-2,5-dienyl)-10-hydroxy-16-methoxy-18-(4-methoxy-benzyloxy)-9,17,19,21,23-pentamethyl-20-triisopropylsilanyloxy-15-(2-trimethylsilanyl-ethoxymethoxy)-13-oxa-1,5-dithia-spiro[5.17]tricos-21-en-14-one

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Technology Process of 11-(2,4-dimethyl-1-triethylsilanyloxy-hepta-2,5-dienyl)-10-hydroxy-16-methoxy-18-(4-methoxy-benzyloxy)-9,17,19,21,23-pentamethyl-20-triisopropylsilanyloxy-15-(2-trimethylsilanyl-ethoxymethoxy)-13-oxa-1,5-dithia-spiro[5.17]tricos-21-en-14-one

There total 30 articles about 11-(2,4-dimethyl-1-triethylsilanyloxy-hepta-2,5-dienyl)-10-hydroxy-16-methoxy-18-(4-methoxy-benzyloxy)-9,17,19,21,23-pentamethyl-20-triisopropylsilanyloxy-15-(2-trimethylsilanyl-ethoxymethoxy)-13-oxa-1,5-dithia-spiro[5.17]tricos-21-en-14-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:

(2-trimethylethylsilylethoxy)methyl chloride (76513-69-4) → 11-(2,4-dimethyl-1-triethylsilanyloxy-hepta-2,5-dienyl)-10-hydroxy-16-methoxy-18-(4-methoxy-benzyloxy)-9,17,19,21,23-pentamethyl-20-triisopropylsilanyloxy-15-(2-trimethylsilanyl-ethoxymethoxy)-13-oxa-1,5-dithia-spiro[5.17]tricos-21-en-14-one (777096-58-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: TBAI; DIEA / CH₂Cl₂

2.1: K₂CO₃ / methanol

3.1: t-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.07 h / -78 °C

3.2: 75 percent / tetrahydrofuran / 0.17 h

4.1: SO₃*pyr; DMSO

5.1: 80 percent / SmI₂ / tetrahydrofuran / -10 °C

6.1: PPTs / methanol

7.1: aq. LiOH / tetrahydrofuran / Heating

8.1: 2,4,5-trichlorobenzoyl chloride; DIEA / tetrahydrofuran

8.2: DMAP / toluene

9.1: dimethylformamide

With lithium hydroxide; samarium diiodide; pyridine-SO₃ complex; tert.-butyl lithium; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; potassium carbonate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; 2,4,6-trichlorobenzoyl chloride; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; N,N-dimethyl-formamide; 4.1: Parikh-Doering oxidation / 5.1: Evans-Tischenko reduction;

DOI:10.1021/ja0289649

Reference yield:

(E)-(R)-5-(4-Methoxy-benzyloxy)-2,4-dimethyl-pent-2-en-1-ol (220213-54-7) → 11-(2,4-dimethyl-1-triethylsilanyloxy-hepta-2,5-dienyl)-10-hydroxy-16-methoxy-18-(4-methoxy-benzyloxy)-9,17,19,21,23-pentamethyl-20-triisopropylsilanyloxy-15-(2-trimethylsilanyl-ethoxymethoxy)-13-oxa-1,5-dithia-spiro[5.17]tricos-21-en-14-one (777096-58-9)

Guidance literature:

Multi-step reaction with 24 steps

1.1: DMSO; (COCl)2; NEt₃ / -78 - 20 °C

2.1: Bu₂BOTf; Et₃N

3.1: 2,6-lutidine

4.1: LiBH₄ / methanol; diethyl ether

5.1: DMAP; Et₃N

6.1: OsO₄; NMO

7.1: aq. NaIO₄

8.1: 97 percent / toluene / 17 h / -78 °C

9.1: K₂CO₃ / methanol

10.1: PPTs / acetone

11.1: 9-BBN / tetrahydrofuran; diethyl ether

11.2: aq. H₂O₂; NaOH / tetrahydrofuran; diethyl ether

12.1: Et₃N

13.1: DDQ / H₂O

14.1: Dess-Martin periodinane

15.1: K₂CO₃ / methanol

16.1: 92 percent / (PhO)3PCH₃I; DIEA / tetrahydrofuran / 0.42 h

17.1: t-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.07 h / -78 °C

17.2: 75 percent / tetrahydrofuran / 0.17 h

18.1: SO₃*pyr; DMSO

19.1: 80 percent / SmI₂ / tetrahydrofuran / -10 °C

20.1: PPTs / methanol

21.1: aq. LiOH / tetrahydrofuran / Heating

22.1: 2,4,5-trichlorobenzoyl chloride; DIEA / tetrahydrofuran

22.2: DMAP / toluene

23.1: dimethylformamide

With 2,6-dimethylpyridine; dmap; lithium hydroxide; sodium periodate; osmium(VIII) oxide; lithium borohydride; 9-borabicyclo[3.3.1]nonane dimer; N-methyl-2-indolinone; samarium diiodide; oxalyl dichloride; pyridine-SO₃ complex; di-n-butylboryl trifluoromethanesulfonate; methyltriphenoxyphosphonium iodide; tert.-butyl lithium; pyridinium p-toluenesulfonate; potassium carbonate; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 2,4,6-trichlorobenzoyl chloride; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; water; N,N-dimethyl-formamide; acetone; toluene; 1.1: Swern oxidation / 8.1: Roush crotylation / 14.1: Dess-Martin oxidation / 15.1: Wittig olefination / 19.1: Parikh-Doering oxidation / 20.1: Evans-Tischenko reduction;

DOI:10.1021/ja0289649

Reference yield:

(E)-(R)-5-(4-Methoxy-benzyloxy)-2,4-dimethyl-pent-2-enal (648883-76-5) → 11-(2,4-dimethyl-1-triethylsilanyloxy-hepta-2,5-dienyl)-10-hydroxy-16-methoxy-18-(4-methoxy-benzyloxy)-9,17,19,21,23-pentamethyl-20-triisopropylsilanyloxy-15-(2-trimethylsilanyl-ethoxymethoxy)-13-oxa-1,5-dithia-spiro[5.17]tricos-21-en-14-one (777096-58-9)

Guidance literature:

Multi-step reaction with 23 steps

1.1: Bu₂BOTf; Et₃N

2.1: 2,6-lutidine

3.1: LiBH₄ / methanol; diethyl ether

4.1: DMAP; Et₃N

5.1: OsO₄; NMO

6.1: aq. NaIO₄

7.1: 97 percent / toluene / 17 h / -78 °C

8.1: K₂CO₃ / methanol

9.1: PPTs / acetone

10.1: 9-BBN / tetrahydrofuran; diethyl ether

10.2: aq. H₂O₂; NaOH / tetrahydrofuran; diethyl ether

11.1: Et₃N

12.1: DDQ / H₂O

13.1: Dess-Martin periodinane

14.1: K₂CO₃ / methanol

15.1: 92 percent / (PhO)3PCH₃I; DIEA / tetrahydrofuran / 0.42 h

16.1: t-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.07 h / -78 °C

16.2: 75 percent / tetrahydrofuran / 0.17 h

17.1: SO₃*pyr; DMSO

18.1: 80 percent / SmI₂ / tetrahydrofuran / -10 °C

19.1: PPTs / methanol

20.1: aq. LiOH / tetrahydrofuran / Heating

21.1: 2,4,5-trichlorobenzoyl chloride; DIEA / tetrahydrofuran

21.2: DMAP / toluene

22.1: dimethylformamide

With 2,6-dimethylpyridine; dmap; lithium hydroxide; sodium periodate; osmium(VIII) oxide; lithium borohydride; 9-borabicyclo[3.3.1]nonane dimer; N-methyl-2-indolinone; samarium diiodide; pyridine-SO₃ complex; di-n-butylboryl trifluoromethanesulfonate; methyltriphenoxyphosphonium iodide; tert.-butyl lithium; pyridinium p-toluenesulfonate; potassium carbonate; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 2,4,6-trichlorobenzoyl chloride; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; water; N,N-dimethyl-formamide; acetone; toluene; 7.1: Roush crotylation / 13.1: Dess-Martin oxidation / 14.1: Wittig olefination / 18.1: Parikh-Doering oxidation / 19.1: Evans-Tischenko reduction;

DOI:10.1021/ja0289649

upstream raw materials:

triethylsilyl chloride

10-hydroxy-11-(1-hydroxy-2,4-dimethyl-hepta-2,5-dienyl)-16-methoxy-18-(4-methoxy-benzyloxy)-9,17,19,21,23-pentamethyl-20-triisopropylsilanyloxy-15-(2-trimethylsilanyl-ethoxymethoxy)-13-oxa-1,5-dithia-spiro[5.17]tricos-21-en-14-one

(2-trimethylethylsilylethoxy)methyl chloride

(E)-(R)-5-(4-Methoxy-benzyloxy)-2,4-dimethyl-pent-2-en-1-ol

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