(2R,3R,3aR,6S,7S,7aR)-7-azido-6-methoxy-6-methyl-2-phenylsulfanyl-3-pivaloyloxy-hexahydrofuro[3,2-b]pyran

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Chemical Name:(2R,3R,3aR,6S,7S,7aR)-7-azido-6-methoxy-6-methyl-2-phenylsulfanyl-3-pivaloyloxy-hexahydrofuro[3,2-b]pyran
CAS No.:864941-73-1
Molecular Formula:C₂₀H₂₇N₃O₅S
Molecular Weight:421.517
Hs Code.:

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Chemical Property of (2R,3R,3aR,6S,7S,7aR)-7-azido-6-methoxy-6-methyl-2-phenylsulfanyl-3-pivaloyloxy-hexahydrofuro[3,2-b]pyran

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Technology Process of (2R,3R,3aR,6S,7S,7aR)-7-azido-6-methoxy-6-methyl-2-phenylsulfanyl-3-pivaloyloxy-hexahydrofuro[3,2-b]pyran

There total 10 articles about (2R,3R,3aR,6S,7S,7aR)-7-azido-6-methoxy-6-methyl-2-phenylsulfanyl-3-pivaloyloxy-hexahydrofuro[3,2-b]pyran 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:

: 828914-86-9
C₁₀H₁₄O₅

: 864941-73-1
(2R,3R,3aR,6S,7S,7aR)-7-azido-6-methoxy-6-methyl-2-phenylsulfanyl-3-pivaloyloxy-hexahydrofuro[3,2-b]pyran

Guidance literature:: Multi-step reaction with 7 steps

1: 1.14 g / sodium azide / 2-methoxy-ethanol / 1 h / 126 °C

2: Dess-Martin periodinane / CH₂Cl₂ / 2.5 h / 20 °C

3: 115 mg / tetrahydrofuran; diethyl ether / -78 - 20 °C

4: 75 percent / NaH / dimethylformamide; various solvent(s) / 0 - 20 °C

5: 80 percent / Amberlyst-15 / CH₂Cl₂ / 18 h / 20 °C

6: N-bromosuccinimide / CH₂Cl₂ / 0.75 h / 0 °C

7: pyridine; 4-(dimethylamino)pyridine / 18 h / 20 °C

With pyridine; dmap; N-Bromosuccinimide; sodium azide; amberlyst-15; sodium hydride; Dess-Martin periodane; In tetrahydrofuran; diethyl ether; dichloromethane; 2-methoxy-ethanol; N,N-dimethyl-formamide;
DOI:10.1021/jo050727b

Reference yield:

: 828914-88-1
(3aR,3bR,7S,7aR,8aR)-7-Azido-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5]furo[3,2-b]pyran-6-one

: 864941-73-1
(2R,3R,3aR,6S,7S,7aR)-7-azido-6-methoxy-6-methyl-2-phenylsulfanyl-3-pivaloyloxy-hexahydrofuro[3,2-b]pyran

Guidance literature:: Multi-step reaction with 5 steps

1: 115 mg / tetrahydrofuran; diethyl ether / -78 - 20 °C

2: 75 percent / NaH / dimethylformamide; various solvent(s) / 0 - 20 °C

3: 80 percent / Amberlyst-15 / CH₂Cl₂ / 18 h / 20 °C

4: N-bromosuccinimide / CH₂Cl₂ / 0.75 h / 0 °C

5: pyridine; 4-(dimethylamino)pyridine / 18 h / 20 °C

With pyridine; dmap; N-Bromosuccinimide; amberlyst-15; sodium hydride; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo050727b

Reference yield:

: 828914-85-8
(3aR,3bS,6S,7R,7aS,8aR)-7-Bromo-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[3,2-b]pyran-6-ol

: 864941-73-1
(2R,3R,3aR,6S,7S,7aR)-7-azido-6-methoxy-6-methyl-2-phenylsulfanyl-3-pivaloyloxy-hexahydrofuro[3,2-b]pyran

Guidance literature:: Multi-step reaction with 8 steps

1: sodium hydroxide / tetrahydrofuran / 1 h / 110 °C

2: 1.14 g / sodium azide / 2-methoxy-ethanol / 1 h / 126 °C

3: Dess-Martin periodinane / CH₂Cl₂ / 2.5 h / 20 °C

4: 115 mg / tetrahydrofuran; diethyl ether / -78 - 20 °C

5: 75 percent / NaH / dimethylformamide; various solvent(s) / 0 - 20 °C

6: 80 percent / Amberlyst-15 / CH₂Cl₂ / 18 h / 20 °C

7: N-bromosuccinimide / CH₂Cl₂ / 0.75 h / 0 °C

8: pyridine; 4-(dimethylamino)pyridine / 18 h / 20 °C

With pyridine; dmap; sodium hydroxide; N-Bromosuccinimide; sodium azide; amberlyst-15; sodium hydride; Dess-Martin periodane; In tetrahydrofuran; diethyl ether; dichloromethane; 2-methoxy-ethanol; N,N-dimethyl-formamide;
DOI:10.1021/jo050727b