2-((2S,3S,4S,5S)-2,4,6-Tris-benzyloxy-3,5-dimethyl-hexyl)-[1,3]dithiane

Base Information

Chemical Name:2-((2S,3S,4S,5S)-2,4,6-Tris-benzyloxy-3,5-dimethyl-hexyl)-[1,3]dithiane
CAS No.:936494-93-8
Molecular Formula:C₃₃H₄₂O₃S₂
Molecular Weight:550.827
Hs Code.:

Synonyms:2-((2S,3S,4S,5S)-2,4,6-Tris-benzyloxy-3,5-dimethyl-hexyl)-[1,3]dithiane

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 2-((2S,3S,4S,5S)-2,4,6-Tris-benzyloxy-3,5-dimethyl-hexyl)-[1,3]dithiane

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Technology Process of 2-((2S,3S,4S,5S)-2,4,6-Tris-benzyloxy-3,5-dimethyl-hexyl)-[1,3]dithiane

There total 11 articles about 2-((2S,3S,4S,5S)-2,4,6-Tris-benzyloxy-3,5-dimethyl-hexyl)-[1,3]dithiane 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: 88.0%

: 100-39-0
benzyl bromide

: 936494-92-7
(2S,3S,4S,5S)-4,6-Bis-benzyloxy-1-[1,3]dithian-2-yl-3,5-dimethyl-hexan-2-ol

: 936494-93-8
2-((2S,3S,4S,5S)-2,4,6-Tris-benzyloxy-3,5-dimethyl-hexyl)-[1,3]dithiane

Guidance literature:: With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; Ambient temperature;
DOI:10.1021/ja00095a071

Reference yield:

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

: 936494-93-8
2-((2S,3S,4S,5S)-2,4,6-Tris-benzyloxy-3,5-dimethyl-hexyl)-[1,3]dithiane

Guidance literature:: Multi-step reaction with 11 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

With pyridine; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; copper(l) iodide; n-butyllithium; oxalyl dichloride; potassium tert-butylate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; (-)-diethyl tartrate; triethylamine; 4 A molecular sieve; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; hexane; dichloromethane; toluene; 1.1: Swern oxidation;
DOI:10.1016/j.tet.2007.02.011

Reference yield:

: 114925-44-9
*S^*)>-α,2,2-trimethyl-1,3-dioxolane-4-acetaldehyde

: 936494-93-8
2-((2S,3S,4S,5S)-2,4,6-Tris-benzyloxy-3,5-dimethyl-hexyl)-[1,3]dithiane

Guidance literature:: Multi-step reaction with 10 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

With pyridine; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; copper(l) iodide; n-butyllithium; potassium tert-butylate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; (-)-diethyl tartrate; 4 A molecular sieve; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; hexane; dichloromethane; toluene;
DOI:10.1016/j.tet.2007.02.011