(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

Base Information

• Chemical Name: (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
• CAS No.: 936495-28-2
• Molecular Formula: C₂₉H₅₂O₅Si
• Molecular Weight: 508.814
• Mol file: 936495-28-2.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 23 articles about (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 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: 60.0%

5-benzenesulfonyl-2-benzyloxy-6-{6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-heptan-3-ol (936495-26-0) → (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)

Guidance literature:

With sodium amalgam; camphor-10-sulfonic acid; In methanol; at 0 ℃; for 3h;

DOI:10.1016/j.tet.2007.02.011

Reference yield:

(2S,3S,6S)-7-Benzenesulfonyl-2-benzyloxy-6-{(4R,5S,6S)-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-heptan-3-ol (158705-23-8) → (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)

Guidance literature:

With disodium hydrogenphosphate; sodium amalgam; In methanol; at 0 ℃;

DOI:10.1021/ja00095a071

Reference yield:

*R*)>-α,2,2-trimethyl-1,3-dioxolane-4-ethanol (74243-89-3) → (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)

Guidance literature:

Multi-step reaction with 22 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

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

upstream raw materials:

(2S,3S,6S)-7-Benzenesulfonyl-2-benzyloxy-6-{(4R,5S,6S)-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

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

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

Downstream 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

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

C₃₁H₄₂Br₂N₂O₇