{2-[(4S,5S,6S)-6-((1S,4S,5S)-5-Benzyloxy-4-methoxy-1-methyl-hexyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-ethoxy}-tert-butyl-dimethyl-silane

Base Information

• Chemical Name: {2-[(4S,5S,6S)-6-((1S,4S,5S)-5-Benzyloxy-4-methoxy-1-methyl-hexyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-ethoxy}-tert-butyl-dimethyl-silane
• CAS No.: 936495-29-3
• Molecular Formula: C₃₀H₅₄O₅Si
• Molecular Weight: 522.841
• Mol file: 936495-29-3.mol

Synonyms:{2-[(4S,5S,6S)-6-((1S,4S,5S)-5-Benzyloxy-4-methoxy-1-methyl-hexyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-ethoxy}-tert-butyl-dimethyl-silane

Chemical Property of {2-[(4S,5S,6S)-6-((1S,4S,5S)-5-Benzyloxy-4-methoxy-1-methyl-hexyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-ethoxy}-tert-butyl-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {2-[(4S,5S,6S)-6-((1S,4S,5S)-5-Benzyloxy-4-methoxy-1-methyl-hexyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-ethoxy}-tert-butyl-dimethyl-silane

There total 23 articles about {2-[(4S,5S,6S)-6-((1S,4S,5S)-5-Benzyloxy-4-methoxy-1-methyl-hexyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-ethoxy}-tert-butyl-dimethyl-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: 78.0%

(2S,3S,6S)-2-Benzyloxy-6-{(4S,5S,6S)-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-heptan-3-ol (936495-28-2) + methyl iodide (74-88-4) → {2-[(4S,5S,6S)-6-((1S,4S,5S)-5-Benzyloxy-4-methoxy-1-methyl-hexyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-ethoxy}-tert-butyl-dimethyl-silane (936495-29-3)

Guidance literature:

(2S,3S,6S)-2-Benzyloxy-6-{(4S,5S,6S)-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-heptan-3-ol; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 0.166667h;

methyl iodide; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1016/j.tet.2007.02.011

Reference yield:

*R*)>-α,2,2-trimethyl-1,3-dioxolane-4-ethanol (74243-89-3) → {2-[(4S,5S,6S)-6-((1S,4S,5S)-5-Benzyloxy-4-methoxy-1-methyl-hexyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-ethoxy}-tert-butyl-dimethyl-silane (936495-29-3)

Guidance literature:

Multi-step reaction with 23 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

20.1: 82 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 3 h / 20 °C

21.1: BuLi / tetrahydrofuran; hexane / 1.5 h / -78 - 0 °C

21.2: 21 percent / HMPA / tetrahydrofuran; hexane / 3 h / 20 °C

22.1: 60 percent / NaHPO₄; sodium amalgam / methanol / 3 h / 0 °C

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

23.2: 78 percent / tetrahydrofuran / 3 h / 20 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; sodium tetrahydroborate; sodium amalgam; copper(l) iodide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; tributylphosphine; camphor-10-sulfonic acid; potassium tert-butylate; ammonia; lithium; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; (-)-diethyl tartrate; (+)-10-camphorsulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic 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; 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) → {2-[(4S,5S,6S)-6-((1S,4S,5S)-5-Benzyloxy-4-methoxy-1-methyl-hexyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-ethoxy}-tert-butyl-dimethyl-silane (936495-29-3)

Guidance literature:

Multi-step reaction with 22 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

19.1: 82 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 3 h / 20 °C

20.1: BuLi / tetrahydrofuran; hexane / 1.5 h / -78 - 0 °C

20.2: 21 percent / HMPA / tetrahydrofuran; hexane / 3 h / 20 °C

21.1: 60 percent / NaHPO₄; sodium amalgam / methanol / 3 h / 0 °C

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

22.2: 78 percent / tetrahydrofuran / 3 h / 20 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; sodium tetrahydroborate; sodium amalgam; copper(l) iodide; lithium aluminium tetrahydride; n-butyllithium; tributylphosphine; camphor-10-sulfonic acid; potassium tert-butylate; ammonia; lithium; sodium hydride; diisobutylaluminium hydride; potassium carbonate; (-)-diethyl tartrate; (+)-10-camphorsulfonic acid; 3-chloro-benzenecarboperoxoic 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:

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

methyl iodide

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

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

Downstream raw materials:

C₃₁H₄₂Br₂N₂O₇

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