(4R,4aR,7S,8R,8aR)-8-Azido-4-(bis-phenylsulfanyl-methyl)-7-methoxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Base Information

Chemical Name:(4R,4aR,7S,8R,8aR)-8-Azido-4-(bis-phenylsulfanyl-methyl)-7-methoxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine
CAS No.:864941-84-4
Molecular Formula:C₂₃H₂₇N₃O₄S₂
Molecular Weight:473.617
Hs Code.:

Synonyms:(4R,4aR,7S,8R,8aR)-8-Azido-4-(bis-phenylsulfanyl-methyl)-7-methoxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine

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Chemical Property of (4R,4aR,7S,8R,8aR)-8-Azido-4-(bis-phenylsulfanyl-methyl)-7-methoxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine

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Technology Process of (4R,4aR,7S,8R,8aR)-8-Azido-4-(bis-phenylsulfanyl-methyl)-7-methoxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine

There total 19 articles about (4R,4aR,7S,8R,8aR)-8-Azido-4-(bis-phenylsulfanyl-methyl)-7-methoxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine 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: 93.0%

: 864941-67-3
(4R,4aR,7S,8R,8aR)-8-Azido-4-(bis-phenylsulfanyl-methyl)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

: 74-88-4
methyl iodide

: 864941-84-4
(4R,4aR,7S,8R,8aR)-8-Azido-4-(bis-phenylsulfanyl-methyl)-7-methoxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃;
DOI:10.1021/jo050727b

Reference yield: 56.0%

: 828914-90-5
(2R,3R,3bR,6S,7R,7aR)-7-azido-6-methoxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[3,2-b]pyran

: 108-98-5
thiophenol

: 864941-84-4
(4R,4aR,7S,8R,8aR)-8-Azido-4-(bis-phenylsulfanyl-methyl)-7-methoxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine

: 828914-54-1
(1'R,2R,3R,4S,5S)-4-azido-2-(1'-hydroxy-2',2'-bis-phenylsulfanylethyl)-5-methoxy-tetrahydropyran-3-ol

Guidance literature:: With Amberlyst-15; In dichloromethane; at 5 ℃;
DOI:10.1021/op0600299

Reference yield:

: (3R,4R,5S)-4-Azido-3,5-dihydroxy-tetrahydro-pyran-2-carbonitrile

: 864941-84-4
(4R,4aR,7S,8R,8aR)-8-Azido-4-(bis-phenylsulfanyl-methyl)-7-methoxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Guidance literature:: Multi-step reaction with 10 steps

1.1: sodium hydroxide / methanol; H₂O / 3 h / 45 °C

2.1: 2.72 g / TMSCl / 13 h / 20 °C

3.1: 95 percent / imidazole / CH₂Cl₂ / 15 h / 20 °C

4.1: AlMe₃ / CH₂Cl₂; toluene / 0.67 h / 0 °C

4.2: 68 percent / CH₂Cl₂; toluene / 22 h / 0 - 20 °C

5.1: DIBAL-H / toluene; hexane / 2 h / -78 °C

6.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 2 h / 20 °C

7.1: BuLi / tetrahydrofuran; hexane / 0.42 h / -10 °C

7.2: 161 mg / tetrahydrofuran; hexane / 0.5 h / -78 °C

8.1: 91 percent / molecular sieves 4 Angstroem; TBAF / tetrahydrofuran / 16 h / 20 °C

9.1: 81 percent / PTSA; Na₂SO₄ / CH₂Cl₂ / 4 h / 20 °C

10.1: 93 percent / NaH / dimethylformamide / 0 °C

With 1H-imidazole; sodium hydroxide; n-butyllithium; chloro-trimethyl-silane; 4 A molecular sieve; tetrabutyl ammonium fluoride; trimethylaluminum; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; sodium sulfate; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo050727b