(2R,3S,6S,8R,10S)-8-[(2E,6E)-(4S,5S)-8-Benzenesulfonyl-3,5-dimethyl-4-(2-trimethylsilanyl-ethoxymethoxy)-octa-2,6-dienyl]-2-((S)-sec-butyl)-10-(tert-butyl-dimethyl-silanyloxy)-3-methyl-1,7-dioxa-spiro[5.5]undec-4-ene

Base Information

• Chemical Name: (2R,3S,6S,8R,10S)-8-[(2E,6E)-(4S,5S)-8-Benzenesulfonyl-3,5-dimethyl-4-(2-trimethylsilanyl-ethoxymethoxy)-octa-2,6-dienyl]-2-((S)-sec-butyl)-10-(tert-butyl-dimethyl-silanyloxy)-3-methyl-1,7-dioxa-spiro[5.5]undec-4-ene
• CAS No.: 125024-28-4
• Molecular Formula: C₄₂H₇₂O₇SSi₂
• Molecular Weight: 777.266

Synonyms:(2R,3S,6S,8R,10S)-8-[(2E,6E)-(4S,5S)-8-Benzenesulfonyl-3,5-dimethyl-4-(2-trimethylsilanyl-ethoxymethoxy)-octa-2,6-dienyl]-2-((S)-sec-butyl)-10-(tert-butyl-dimethyl-silanyloxy)-3-methyl-1,7-dioxa-spiro[5.5]undec-4-ene

Chemical Property of (2R,3S,6S,8R,10S)-8-[(2E,6E)-(4S,5S)-8-Benzenesulfonyl-3,5-dimethyl-4-(2-trimethylsilanyl-ethoxymethoxy)-octa-2,6-dienyl]-2-((S)-sec-butyl)-10-(tert-butyl-dimethyl-silanyloxy)-3-methyl-1,7-dioxa-spiro[5.5]undec-4-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,6S,8R,10S)-8-[(2E,6E)-(4S,5S)-8-Benzenesulfonyl-3,5-dimethyl-4-(2-trimethylsilanyl-ethoxymethoxy)-octa-2,6-dienyl]-2-((S)-sec-butyl)-10-(tert-butyl-dimethyl-silanyloxy)-3-methyl-1,7-dioxa-spiro[5.5]undec-4-ene

There total 52 articles about (2R,3S,6S,8R,10S)-8-[(2E,6E)-(4S,5S)-8-Benzenesulfonyl-3,5-dimethyl-4-(2-trimethylsilanyl-ethoxymethoxy)-octa-2,6-dienyl]-2-((S)-sec-butyl)-10-(tert-butyl-dimethyl-silanyloxy)-3-methyl-1,7-dioxa-spiro[5.5]undec-4-ene 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: 84.0%

(2R,3S,6S,8R,10S)-2-((S)-sec-Butyl)-10-(tert-butyl-dimethyl-silanyloxy)-8-[(2E,6E)-(4S,5S)-8-chloro-3,5-dimethyl-4-(2-trimethylsilanyl-ethoxymethoxy)-octa-2,6-dienyl]-3-methyl-1,7-dioxa-spiro[5.5]undec-4-ene (125024-27-3) + sodium benzenesulfonate (873-55-2) → (2R,3S,6S,8R,10S)-8-[(2E,6E)-(4S,5S)-8-Benzenesulfonyl-3,5-dimethyl-4-(2-trimethylsilanyl-ethoxymethoxy)-octa-2,6-dienyl]-2-((S)-sec-butyl)-10-(tert-butyl-dimethyl-silanyloxy)-3-methyl-1,7-dioxa-spiro[5.5]undec-4-ene (125024-28-4)

Guidance literature:

In N,N-dimethyl-formamide; at 25 ℃; for 48h;

DOI:10.1021/ja00160a051

Reference yield:

(2S)-2-methyl-1-butanol (1565-80-6) → (2R,3S,6S,8R,10S)-8-[(2E,6E)-(4S,5S)-8-Benzenesulfonyl-3,5-dimethyl-4-(2-trimethylsilanyl-ethoxymethoxy)-octa-2,6-dienyl]-2-((S)-sec-butyl)-10-(tert-butyl-dimethyl-silanyloxy)-3-methyl-1,7-dioxa-spiro[5.5]undec-4-ene (125024-28-4)

Guidance literature:

Multi-step reaction with 28 steps

1: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -65 deg C, 15 min, 2.) CH₂Cl₂, RT

2: 53 percent / CrCl₃, LiAlH₄ / tetrahydrofuran / 3 h / Ambient temperature

3: 86 percent / CH₂Cl₂ / 3 h

4: 1.) O₃, 2.) Me₂S / 1.) CH₃OH, -78 deg C, 10 min, 2.) CH₃OH, RT, 12 h

5: 1.) Zn, 2.) Ph₃P / 1.) CH₂Cl₂, 30 min, 2.) CH₂Cl₂, 4 h

6: 86 percent / n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 - 20 °C

7: 1.) EtMgBr / 1.) THF, ether, from 0 deg C to RT, 2.) THF, ether, -78 deg C, 15 min

8: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 0.5 h, 2.) CH₂Cl₂, from -78 deg C to RT

9: 88 percent / camphorsulfonic acid / 3 h / Ambient temperature

10: 86 percent / (n-Bu)4NF / tetrahydrofuran / 1 h / 50 °C

11: H₂ / Pd/BaSO₄ / methanol; quinoline / 0.5 h

12: camphorsulfonic acid / quinoline; diethyl ether / 0.25 h / Ambient temperature

13: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) CH₂Cl₂, from -78 deg C to RT

14: 1.) LDA / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, -78 deg C, 30 min

15: Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 1.5 h

16: 1,8-diazabicyclo<5.4.0>undec-7-ene / CH₂Cl₂ / 1 h / 0 °C

17: 93 percent / tetrahydrofuran / 0.5 h / 0 °C

18: 87 percent / Et₃N / CH₂Cl₂ / -78 °C

19: 88 percent / oxone / methanol; H₂O / 24 h / Ambient temperature

20: 92 percent / ceric ammonium nitrate / acetonitrile; H₂O / 1 h / Ambient temperature

21: 75 percent / 2,6-lutidine / CH₂Cl₂ / 0.17 h / 0 °C

22: 77 percent / LiAlH₄ / tetrahydrofuran / 0.25 h / 0 °C

23: 35 percent / sodium amalgam, Na₂HPO₄ / methanol / 2 h / Ambient temperature

24: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) CH₂Cl₂, from -78 deg C to RT

25: 98 percent / toluene / 3 h / Heating

26: 94 percent / diisobutylaluminum hydride / toluene; hexane / 0.5 h / -78 °C

27: 93 percent / N-chlorosuccinimide / CH₂Cl₂; various solvent(s) / 0.5 h / 0 - 20 °C

28: 84 percent / dimethylformamide / 42 h / Ambient temperature

With 2,6-dimethylpyridine; dmap; chromium chloride; Oxone; disodium hydrogenphosphate; sodium amalgam; N-chloro-succinimide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; ammonium cerium(IV) nitrate; dimethylsulfide; camphor-10-sulfonic acid; ethylmagnesium bromide; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; ozone; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; zinc; lithium diisopropyl amide; Pd-BaSO₄; In tetrahydrofuran; quinoline; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/ja00112a006

Reference yield:

(S)-2-methylbutyraldehyde (1730-97-8) → (2R,3S,6S,8R,10S)-8-[(2E,6E)-(4S,5S)-8-Benzenesulfonyl-3,5-dimethyl-4-(2-trimethylsilanyl-ethoxymethoxy)-octa-2,6-dienyl]-2-((S)-sec-butyl)-10-(tert-butyl-dimethyl-silanyloxy)-3-methyl-1,7-dioxa-spiro[5.5]undec-4-ene (125024-28-4)

Guidance literature:

Multi-step reaction with 27 steps

1: 53 percent / CrCl₃, LiAlH₄ / tetrahydrofuran / 3 h / Ambient temperature

2: 86 percent / CH₂Cl₂ / 3 h

3: 1.) O₃, 2.) Me₂S / 1.) CH₃OH, -78 deg C, 10 min, 2.) CH₃OH, RT, 12 h

4: 1.) Zn, 2.) Ph₃P / 1.) CH₂Cl₂, 30 min, 2.) CH₂Cl₂, 4 h

5: 86 percent / n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 - 20 °C

6: 1.) EtMgBr / 1.) THF, ether, from 0 deg C to RT, 2.) THF, ether, -78 deg C, 15 min

7: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 0.5 h, 2.) CH₂Cl₂, from -78 deg C to RT

8: 88 percent / camphorsulfonic acid / 3 h / Ambient temperature

9: 86 percent / (n-Bu)4NF / tetrahydrofuran / 1 h / 50 °C

10: H₂ / Pd/BaSO₄ / methanol; quinoline / 0.5 h

11: camphorsulfonic acid / quinoline; diethyl ether / 0.25 h / Ambient temperature

12: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) CH₂Cl₂, from -78 deg C to RT

13: 1.) LDA / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, -78 deg C, 30 min

14: Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 1.5 h

15: 1,8-diazabicyclo<5.4.0>undec-7-ene / CH₂Cl₂ / 1 h / 0 °C

16: 93 percent / tetrahydrofuran / 0.5 h / 0 °C

17: 87 percent / Et₃N / CH₂Cl₂ / -78 °C

18: 88 percent / oxone / methanol; H₂O / 24 h / Ambient temperature

19: 92 percent / ceric ammonium nitrate / acetonitrile; H₂O / 1 h / Ambient temperature

20: 75 percent / 2,6-lutidine / CH₂Cl₂ / 0.17 h / 0 °C

21: 77 percent / LiAlH₄ / tetrahydrofuran / 0.25 h / 0 °C

22: 35 percent / sodium amalgam, Na₂HPO₄ / methanol / 2 h / Ambient temperature

23: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) CH₂Cl₂, from -78 deg C to RT

24: 98 percent / toluene / 3 h / Heating

25: 94 percent / diisobutylaluminum hydride / toluene; hexane / 0.5 h / -78 °C

26: 93 percent / N-chlorosuccinimide / CH₂Cl₂; various solvent(s) / 0.5 h / 0 - 20 °C

27: 84 percent / dimethylformamide / 42 h / Ambient temperature

With 2,6-dimethylpyridine; dmap; chromium chloride; Oxone; disodium hydrogenphosphate; sodium amalgam; N-chloro-succinimide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; ammonium cerium(IV) nitrate; dimethylsulfide; camphor-10-sulfonic acid; ethylmagnesium bromide; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; ozone; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; zinc; lithium diisopropyl amide; Pd-BaSO₄; In tetrahydrofuran; quinoline; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/ja00112a006

upstream raw materials:

(2R,3S,6S,8R,10S)-2-((S)-sec-Butyl)-10-(tert-butyl-dimethyl-silanyloxy)-8-[(2E,6E)-(4S,5S)-8-chloro-3,5-dimethyl-4-(2-trimethylsilanyl-ethoxymethoxy)-octa-2,6-dienyl]-3-methyl-1,7-dioxa-spiro[5.5]undec-4-ene

sodium benzenesulfonate

(E)-ethyl 4-oxo-2-pentenoate

(2S)-2-methyl-1-butanol

Downstream raw materials:

C₆₄H₁₁₀O₁₃SSi₄

C₆₅H₁₁₄O₁₄SSi₄

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