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

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]-ethanol
• CAS No.: 936495-31-7
• Molecular Formula: C₂₄H₄₀O₅
• Molecular Weight: 408.579
• Mol file: 936495-31-7.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]-ethanol

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]-ethanol

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]-ethanol

There total 24 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]-ethanol 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: 100.0%

{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) → 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 (936495-31-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1.5h;

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]-ethanol (936495-31-7)

Guidance literature:

Multi-step reaction with 24 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

24.1: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1.5 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; tetrabutyl ammonium fluoride; 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]-ethanol (936495-31-7)

Guidance literature:

Multi-step reaction with 23 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

23.1: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1.5 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; tetrabutyl ammonium fluoride; 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:

{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

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

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

Downstream raw materials:

C₃₁H₄₂Br₂N₂O₇