tert-Butyl-dimethyl-{2-[(4S,5S,6R)-2,2,5-trimethyl-6-((R)-1-methyl-2-phenylsulfanyl-ethyl)-[1,3]dioxan-4-yl]-ethoxy}-silane

Base Information

• Chemical Name: tert-Butyl-dimethyl-{2-[(4S,5S,6R)-2,2,5-trimethyl-6-((R)-1-methyl-2-phenylsulfanyl-ethyl)-[1,3]dioxan-4-yl]-ethoxy}-silane
• CAS No.: 936494-99-4
• Molecular Formula: C₂₄H₄₂O₃SSi
• Molecular Weight: 438.747
• Mol file: 936494-99-4.mol

Synonyms:tert-Butyl-dimethyl-{2-[(4S,5S,6R)-2,2,5-trimethyl-6-((R)-1-methyl-2-phenylsulfanyl-ethyl)-[1,3]dioxan-4-yl]-ethoxy}-silane

Chemical Property of tert-Butyl-dimethyl-{2-[(4S,5S,6R)-2,2,5-trimethyl-6-((R)-1-methyl-2-phenylsulfanyl-ethyl)-[1,3]dioxan-4-yl]-ethoxy}-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-Butyl-dimethyl-{2-[(4S,5S,6R)-2,2,5-trimethyl-6-((R)-1-methyl-2-phenylsulfanyl-ethyl)-[1,3]dioxan-4-yl]-ethoxy}-silane

There total 19 articles about tert-Butyl-dimethyl-{2-[(4S,5S,6R)-2,2,5-trimethyl-6-((R)-1-methyl-2-phenylsulfanyl-ethyl)-[1,3]dioxan-4-yl]-ethoxy}-silane 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: 96.0%

diphenyldisulfane (882-33-7) + (S)-2-{(4S,5S,6S)-6-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propan-1-ol (158661-81-5) → tert-Butyl-dimethyl-{2-[(4S,5S,6R)-2,2,5-trimethyl-6-((R)-1-methyl-2-phenylsulfanyl-ethyl)-[1,3]dioxan-4-yl]-ethoxy}-silane (936494-99-4)

Guidance literature:

With tributylphosphine; In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1021/ja00095a071

Reference yield:

*R*)>-α,2,2-trimethyl-1,3-dioxolane-4-ethanol (74243-89-3) → tert-Butyl-dimethyl-{2-[(4S,5S,6R)-2,2,5-trimethyl-6-((R)-1-methyl-2-phenylsulfanyl-ethyl)-[1,3]dioxan-4-yl]-ethoxy}-silane (936494-99-4)

Guidance literature:

Multi-step reaction with 19 steps

1.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.83 h / -78 - 20 °C

2.1: KOtBu / tetrahydrofuran / 1 h / 20 °C

2.2: 387 mg / tetrahydrofuran / 1 h / -78 °C

3.1: 88 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 1.17 h / -78 °C

4.1: 70 percent / tert-butyl hydroperoxide; Ti(OiPr)4; (-)-diethyl tartrate / 4 Angstroem molecular sieves / CH₂Cl₂; toluene / 2 h / -23 °C

5.1: CuI / diethyl ether / 0.5 h / -23 °C

5.2: 87 percent / diethyl ether / 1.75 h / -40 - -23 °C

6.1: NaH / tetrahydrofuran / 0.22 h / 0 - 20 °C

6.2: 92 percent / tetrahydrofuran; dimethylformamide / 3 h / 20 °C

7.1: 100 percent / aq. HCl / 1,2-dimethoxy-ethane / 22 h / Heating

8.1: pyridine / 3.5 h / 0 °C

9.1: 1.06 g / K₂CO₃ / methanol / 1.5 h / 0 °C

10.1: BuLi / tetrahydrofuran; hexane / 2 h / -23 °C

10.2: 89 percent / tetrahydrofuran / 1 h / 20 °C

11.1: NaH / tetrahydrofuran / 0.17 h / 20 °C

11.2: 87 percent / tetrahydrofuran; dimethylformamide / 3 h / 20 °C

12.1: 85 percent / CuCl₂; CuO / acetone; H₂O / 1.5 h / Heating

13.1: 97 percent / NaBH₄ / ethanol / 14.5 h / -29 - -20 °C

14.1: 94 percent / imidazole / dimethylformamide / 1.5 h / 20 °C

15.1: 97 percent / liq. NH₃; Li / tetrahydrofuran; propan-2-ol / 6 h / -78 °C

16.1: 95 percent / pyridine / 2 h / 0 °C

17.1: 96 percent / (+)-10-camphorsulfonic acid / acetone / 1 h / 20 °C

18.1: 99 percent / LiAlH₄ / diethyl ether / 0.67 h / 0 °C

19.1: 96 percent / Bu₃P / dimethylformamide / 6.17 h / 0 - 20 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; sodium tetrahydroborate; copper(l) iodide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; tributylphosphine; potassium tert-butylate; ammonia; lithium; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; (-)-diethyl tartrate; (+)-10-camphorsulfonic acid; triethylamine; copper(II) oxide; copper dichloride; 4 A molecular sieve; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; acetone; toluene; 1.1: Swern oxidation;

DOI:10.1016/j.tet.2007.02.011

Reference yield:

*S*)>-α,2,2-trimethyl-1,3-dioxolane-4-acetaldehyde (114925-44-9) → tert-Butyl-dimethyl-{2-[(4S,5S,6R)-2,2,5-trimethyl-6-((R)-1-methyl-2-phenylsulfanyl-ethyl)-[1,3]dioxan-4-yl]-ethoxy}-silane (936494-99-4)

Guidance literature:

Multi-step reaction with 18 steps

1.1: KOtBu / tetrahydrofuran / 1 h / 20 °C

1.2: 387 mg / tetrahydrofuran / 1 h / -78 °C

2.1: 88 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 1.17 h / -78 °C

3.1: 70 percent / tert-butyl hydroperoxide; Ti(OiPr)4; (-)-diethyl tartrate / 4 Angstroem molecular sieves / CH₂Cl₂; toluene / 2 h / -23 °C

4.1: CuI / diethyl ether / 0.5 h / -23 °C

4.2: 87 percent / diethyl ether / 1.75 h / -40 - -23 °C

5.1: NaH / tetrahydrofuran / 0.22 h / 0 - 20 °C

5.2: 92 percent / tetrahydrofuran; dimethylformamide / 3 h / 20 °C

6.1: 100 percent / aq. HCl / 1,2-dimethoxy-ethane / 22 h / Heating

7.1: pyridine / 3.5 h / 0 °C

8.1: 1.06 g / K₂CO₃ / methanol / 1.5 h / 0 °C

9.1: BuLi / tetrahydrofuran; hexane / 2 h / -23 °C

9.2: 89 percent / tetrahydrofuran / 1 h / 20 °C

10.1: NaH / tetrahydrofuran / 0.17 h / 20 °C

10.2: 87 percent / tetrahydrofuran; dimethylformamide / 3 h / 20 °C

11.1: 85 percent / CuCl₂; CuO / acetone; H₂O / 1.5 h / Heating

12.1: 97 percent / NaBH₄ / ethanol / 14.5 h / -29 - -20 °C

13.1: 94 percent / imidazole / dimethylformamide / 1.5 h / 20 °C

14.1: 97 percent / liq. NH₃; Li / tetrahydrofuran; propan-2-ol / 6 h / -78 °C

15.1: 95 percent / pyridine / 2 h / 0 °C

16.1: 96 percent / (+)-10-camphorsulfonic acid / acetone / 1 h / 20 °C

17.1: 99 percent / LiAlH₄ / diethyl ether / 0.67 h / 0 °C

18.1: 96 percent / Bu₃P / dimethylformamide / 6.17 h / 0 - 20 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; sodium tetrahydroborate; copper(l) iodide; lithium aluminium tetrahydride; n-butyllithium; tributylphosphine; potassium tert-butylate; ammonia; lithium; sodium hydride; diisobutylaluminium hydride; potassium carbonate; (-)-diethyl tartrate; (+)-10-camphorsulfonic acid; copper(II) oxide; copper dichloride; 4 A molecular sieve; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; acetone; toluene;

DOI:10.1016/j.tet.2007.02.011

upstream raw materials:

diphenyldisulfane

(S)-2-{(4S,5S,6S)-6-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propan-1-ol

*R^*)>-α,2,2-trimethyl-1,3-dioxolane-4-ethanol

*S^*)>-α,2,2-trimethyl-1,3-dioxolane-4-acetaldehyde

Downstream raw materials:

5-benzenesulfonyl-2-benzyloxy-6-{6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-heptan-3-ol

5-benzenesulfonyl-2-benzyloxy-6-{6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-heptan-3-ol

2-[(4S,5S,6S)-6-((1S,4S,5S)-5-Benzyloxy-4-methoxy-1-methyl-hexyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-ethanol

2-[(4S,5S,6S)-6-((1S,4R,5S)-5-Benzyloxy-4-methoxy-1-methyl-hexyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-ethanol