(1S,2S,3R,6R)-2-azido-6-((R)-1-hydroxy-2,2-bis(phenylthio)ethyl)-3-methoxycyclohexanol

Base Information

Chemical Name:(1S,2S,3R,6R)-2-azido-6-((R)-1-hydroxy-2,2-bis(phenylthio)ethyl)-3-methoxycyclohexanol
CAS No.:896441-75-1
Molecular Formula:C₂₁H₂₅N₃O₃S₂
Molecular Weight:431.58
Hs Code.:

Synonyms:(1S,2S,3R,6R)-2-azido-6-((R)-1-hydroxy-2,2-bis(phenylthio)ethyl)-3-methoxycyclohexanol

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Chemical Property of (1S,2S,3R,6R)-2-azido-6-((R)-1-hydroxy-2,2-bis(phenylthio)ethyl)-3-methoxycyclohexanol

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Technology Process of (1S,2S,3R,6R)-2-azido-6-((R)-1-hydroxy-2,2-bis(phenylthio)ethyl)-3-methoxycyclohexanol

There total 12 articles about (1S,2S,3R,6R)-2-azido-6-((R)-1-hydroxy-2,2-bis(phenylthio)ethyl)-3-methoxycyclohexanol 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: 81.0%

: 896441-70-6
(3aR,4aS,5R,6R,8aR,8bR)-5-azido-octahydro-6-methoxy-2,2-dimethyl-4aH-benzofuro[2,3-d][1,3]dioxole

: 108-98-5
thiophenol

: 896441-75-1
(1S,2S,3R,6R)-2-azido-6-((R)-1-hydroxy-2,2-bis(phenylthio)ethyl)-3-methoxycyclohexanol

Guidance literature:: With amberlyst-15; In dichloromethane; at 5 - 20 ℃;
DOI:10.1016/j.tet.2005.12.066

Reference yield:

: 278182-51-7
(3aR,5R,6R,6aR)-tetrahydro-6-(iodomethyl)-2,2-dimethyl-5-vinyl-5H-furo[2,3-d][1,3]dioxole

: 896441-75-1
(1S,2S,3R,6R)-2-azido-6-((R)-1-hydroxy-2,2-bis(phenylthio)ethyl)-3-methoxycyclohexanol

Guidance literature:: Multi-step reaction with 9 steps

1: 75 percent / AIBN / 2 h / 100 °C

2: 55 percent / Grubbs first generation catalyst / CH₂Cl₂ / 2 h / Heating

3: NBS / tetrahydrofuran; H₂O / 2 h / 20 °C

4: NaOH / tetrahydrofuran; H₂O / 1 h / Heating

5: 1.9 g / sodium azide / 2-methoxy-ethanol / 2 h / 130 °C

6: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 2.5 h / 20 °C

7: NaBH₄ / methanol / 0 - 20 °C

8: 2.5 g / NaH / tetrahydrofuran / 0 - 20 °C

9: 81 percent / Amberlyst-15 / CH₂Cl₂ / 5 - 20 °C

With sodium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; sodium azide; amberlyst-15; 2,2'-azobis(isobutyronitrile); sodium hydride; Dess-Martin periodane; Grubbs catalyst first generation; In tetrahydrofuran; methanol; dichloromethane; 2-methoxy-ethanol; water; 2: Grubbs metathesis / 6: Dess-Martin reaction;
DOI:10.1016/j.tet.2005.12.066

Reference yield:

: 896441-42-2
(3aR,5R,6R,6aR)-6-(but-3-enyl)-tetrahydro-2,2-dimethyl-5-vinyl-5H-furo[2,3-d][1,3]dioxole

: 896441-75-1
(1S,2S,3R,6R)-2-azido-6-((R)-1-hydroxy-2,2-bis(phenylthio)ethyl)-3-methoxycyclohexanol

Guidance literature:: Multi-step reaction with 8 steps

1: 55 percent / Grubbs first generation catalyst / CH₂Cl₂ / 2 h / Heating

2: NBS / tetrahydrofuran; H₂O / 2 h / 20 °C

3: NaOH / tetrahydrofuran; H₂O / 1 h / Heating

4: 1.9 g / sodium azide / 2-methoxy-ethanol / 2 h / 130 °C

5: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 2.5 h / 20 °C

6: NaBH₄ / methanol / 0 - 20 °C

7: 2.5 g / NaH / tetrahydrofuran / 0 - 20 °C

8: 81 percent / Amberlyst-15 / CH₂Cl₂ / 5 - 20 °C

With sodium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; sodium azide; amberlyst-15; sodium hydride; Dess-Martin periodane; Grubbs catalyst first generation; In tetrahydrofuran; methanol; dichloromethane; 2-methoxy-ethanol; water; 1: Grubbs metathesis / 5: Dess-Martin reaction;
DOI:10.1016/j.tet.2005.12.066