1-[(2R,6R,8R,10S,13R)-10-(2-benzyloxy)ethyl-13-(tert-butyldimethylsilyloxy)-13-methyl-1,7,9-trioxadispiro[5.1.5.2]pentadec-2-yl]-2-propanol

Base Information

• Chemical Name: 1-[(2R,6R,8R,10S,13R)-10-(2-benzyloxy)ethyl-13-(tert-butyldimethylsilyloxy)-13-methyl-1,7,9-trioxadispiro[5.1.5.2]pentadec-2-yl]-2-propanol
• CAS No.: 389086-26-4
• Molecular Formula: C₃₁H₅₂O₆Si
• Molecular Weight: 548.836

Synonyms:1-[(2R,6R,8R,10S,13R)-10-(2-benzyloxy)ethyl-13-(tert-butyldimethylsilyloxy)-13-methyl-1,7,9-trioxadispiro[5.1.5.2]pentadec-2-yl]-2-propanol

Chemical Property of 1-[(2R,6R,8R,10S,13R)-10-(2-benzyloxy)ethyl-13-(tert-butyldimethylsilyloxy)-13-methyl-1,7,9-trioxadispiro[5.1.5.2]pentadec-2-yl]-2-propanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[(2R,6R,8R,10S,13R)-10-(2-benzyloxy)ethyl-13-(tert-butyldimethylsilyloxy)-13-methyl-1,7,9-trioxadispiro[5.1.5.2]pentadec-2-yl]-2-propanol

There total 29 articles about 1-[(2R,6R,8R,10S,13R)-10-(2-benzyloxy)ethyl-13-(tert-butyldimethylsilyloxy)-13-methyl-1,7,9-trioxadispiro[5.1.5.2]pentadec-2-yl]-2-propanol 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%

1-[(2R,6R,8R,10S,13R)-10-(2-benzyloxy)ethyl-13-(tert-butyldimethylsilyloxy)-13-methyl-1,7,9-trioxadispiro[5.1.5.2]pentadec-2-yl]-2-propanone (389085-99-8) → 1-[(2R,6R,8R,10S,13R)-10-(2-benzyloxy)ethyl-13-(tert-butyldimethylsilyloxy)-13-methyl-1,7,9-trioxadispiro[5.1.5.2]pentadec-2-yl]-2-propanol (389086-26-4)

Guidance literature:

With methanol; sodium tetrahydroborate; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1016/S0040-4020(02)01379-0

Reference yield:

(S)-4-[2-(4-hydroxybutyl)-1,3-dithian-2-yl]-butane-1,2-diol (389086-04-8) → 1-[(2R,6R,8R,10S,13R)-10-(2-benzyloxy)ethyl-13-(tert-butyldimethylsilyloxy)-13-methyl-1,7,9-trioxadispiro[5.1.5.2]pentadec-2-yl]-2-propanol (389086-26-4)

Guidance literature:

Multi-step reaction with 23 steps

1.1: 75 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 6 h / 20 °C

2.1: 98 percent / imidazole / CH₂Cl₂ / 2 h / 0 - 20 °C

3.1: 87 percent / diisobutylaluminium hydride / CH₂Cl₂; hexane / 2 h / -78 - -20 °C

4.1: 92 percent / pyridine*SO₃; Et₃N / dimethylsulfoxide / 1.25 h / 20 °C

5.1: 92 percent / tetrahydrofuran; diethyl ether / 2 h / -78 - -50 °C

6.1: 93 percent / SO₃*pyridine; Et₃N / dimethylsulfoxide / 1.25 h / 20 °C

7.1: nBuLi; HMDS; ZnCl₂ / hexane; tetrahydrofuran / 1.67 h / -78 - 0 °C

7.2: 98 percent / tetrahydrofuran; hexane / 1.5 h / -78 - -50 °C

8.1: 4-(N,N-dimethylamino)pyridine; pyridine / 20 h / 20 °C

9.1: DBU / CH₂Cl₂ / 1 h / 0 °C

10.1: 91 percent / (Ph₃PCuH)6 / benzene; H₂O / 10 h / 20 °C

11.1: 95 percent / diethyl ether / 1 h / -78 °C

12.1: 93 percent / 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

13.1: 88 percent / Bu₄N⁽¹⁺⁾F^(1-); acetic acid / tetrahydrofuran / 1 h / 0 °C

14.1: 94 percent / SO₃*pyridine; Et₃N / dimethylsulfoxide / 1.5 h / 20 °C

15.1: 98 percent / benzene / 10 h / Heating

16.1: 94 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone; phosphate buffer / CH₂Cl₂; H₂O / 0.33 h / 20 °C / pH 7

17.1: 96 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 1.17 h / 0 °C

18.1: 93 percent / AgNO₃; N-chlorosuccinimide; 2,4,6-collidine / diethyl ether; acetonitrile; H₂O / 0.33 h / 20 °C

19.1: HCl / H₂O; tetrahydrofuran / 1 h / 0 °C

20.1: LiOMe / methanol; tetrahydrofuran / 8 h / -50 °C

21.1: CSA / CH₂Cl₂ / 2 h / 20 °C

22.1: NaOMe / methanol; tetrahydrofuran / 3 h / 20 °C

23.1: 93 percent / NaBH₄; MeOH / CH₂Cl₂ / 2 h / 0 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; 2,4,6-trimethyl-pyridine; hydrogenchloride; methanol; dmap; sodium tetrahydroborate; N-chloro-succinimide; n-butyllithium; phosphate buffer; pyridine-SO₃ complex; hydrido(triphenylphosphine)copper(I) hexamer; camphor-10-sulfonic acid; lithium methanolate; tetrabutyl ammonium fluoride; sodium methylate; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; silver nitrate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc(II) chloride; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; acetonitrile; benzene; 4.1: Parikh-Doering oxidation / 6.1: Parikh-Doering oxidation / 14.1: Parikh-Doering oxidation / 15.1: Wittig olefination / 17.1: Dess-Martin oxidation;

DOI:10.1016/S0040-4020(02)01379-0

Reference yield:

(S)-2-{2-[2-(4-methoxyphenyl)-1,3-dioxolan-4-yl]ethyl}-2-[4-(triethylsilyloxy)butyl]-1,3-dithiane (389085-90-9) → 1-[(2R,6R,8R,10S,13R)-10-(2-benzyloxy)ethyl-13-(tert-butyldimethylsilyloxy)-13-methyl-1,7,9-trioxadispiro[5.1.5.2]pentadec-2-yl]-2-propanol (389086-26-4)

Guidance literature:

Multi-step reaction with 21 steps

1.1: 87 percent / diisobutylaluminium hydride / CH₂Cl₂; hexane / 2 h / -78 - -20 °C

2.1: 92 percent / pyridine*SO₃; Et₃N / dimethylsulfoxide / 1.25 h / 20 °C

3.1: 92 percent / tetrahydrofuran; diethyl ether / 2 h / -78 - -50 °C

4.1: 93 percent / SO₃*pyridine; Et₃N / dimethylsulfoxide / 1.25 h / 20 °C

5.1: nBuLi; HMDS; ZnCl₂ / hexane; tetrahydrofuran / 1.67 h / -78 - 0 °C

5.2: 98 percent / tetrahydrofuran; hexane / 1.5 h / -78 - -50 °C

6.1: 4-(N,N-dimethylamino)pyridine; pyridine / 20 h / 20 °C

7.1: DBU / CH₂Cl₂ / 1 h / 0 °C

8.1: 91 percent / (Ph₃PCuH)6 / benzene; H₂O / 10 h / 20 °C

9.1: 95 percent / diethyl ether / 1 h / -78 °C

10.1: 93 percent / 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

11.1: 88 percent / Bu₄N⁽¹⁺⁾F^(1-); acetic acid / tetrahydrofuran / 1 h / 0 °C

12.1: 94 percent / SO₃*pyridine; Et₃N / dimethylsulfoxide / 1.5 h / 20 °C

13.1: 98 percent / benzene / 10 h / Heating

14.1: 94 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone; phosphate buffer / CH₂Cl₂; H₂O / 0.33 h / 20 °C / pH 7

15.1: 96 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 1.17 h / 0 °C

16.1: 93 percent / AgNO₃; N-chlorosuccinimide; 2,4,6-collidine / diethyl ether; acetonitrile; H₂O / 0.33 h / 20 °C

17.1: HCl / H₂O; tetrahydrofuran / 1 h / 0 °C

18.1: LiOMe / methanol; tetrahydrofuran / 8 h / -50 °C

19.1: CSA / CH₂Cl₂ / 2 h / 20 °C

20.1: NaOMe / methanol; tetrahydrofuran / 3 h / 20 °C

21.1: 93 percent / NaBH₄; MeOH / CH₂Cl₂ / 2 h / 0 °C

With pyridine; 2,6-dimethylpyridine; 2,4,6-trimethyl-pyridine; hydrogenchloride; methanol; dmap; sodium tetrahydroborate; N-chloro-succinimide; n-butyllithium; phosphate buffer; pyridine-SO₃ complex; hydrido(triphenylphosphine)copper(I) hexamer; camphor-10-sulfonic acid; lithium methanolate; tetrabutyl ammonium fluoride; sodium methylate; sulfur trioxide pyridine complex; diisobutylaluminium hydride; Dess-Martin periodane; silver nitrate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc(II) chloride; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; acetonitrile; benzene; 2.1: Parikh-Doering oxidation / 4.1: Parikh-Doering oxidation / 12.1: Parikh-Doering oxidation / 13.1: Wittig olefination / 15.1: Dess-Martin oxidation;

DOI:10.1016/S0040-4020(02)01379-0

upstream raw materials:

1-[(2R,6R,8R,10S,13R)-10-(2-benzyloxy)ethyl-13-(tert-butyldimethylsilyloxy)-13-methyl-1,7,9-trioxadispiro[5.1.5.2]pentadec-2-yl]-2-propanone

(S)-4-[2-(4-hydroxybutyl)-1,3-dithian-2-yl]-butane-1,2-diol

(S)-4-(2-{2-[2-(4-methoxyphenyl)-1,3-dioxolan-4-yl]ethyl}-1,3-dithian-2-yl)-1-butanol

(S)-2-{2-[2-(4-methoxyphenyl)-1,3-dioxolan-4-yl]ethyl}-2-[4-(triethylsilyloxy)butyl]-1,3-dithiane

Downstream raw materials:

1-[(2R,6R,8R,10S,13R)-10-(2-benzyloxy)ethyl-13-hydroxy-13-methyl-1,7,9-trioxadispiro[5.1.5.2]pentadec-2-yl]-2-propanol

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