5-(2-((4S,5R,6S)-6-((2R,3S)-3-methoxybutan-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)ethylsulfonyl)-1-phenyl-1H-tetrazole

Base Information

• Chemical Name: 5-(2-((4S,5R,6S)-6-((2R,3S)-3-methoxybutan-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)ethylsulfonyl)-1-phenyl-1H-tetrazole
• CAS No.: 1415654-67-9
• Molecular Formula: C₂₁H₃₂N₄O₅S
• Molecular Weight: 452.575

Synonyms:5-(2-((4S,5R,6S)-6-((2R,3S)-3-methoxybutan-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)ethylsulfonyl)-1-phenyl-1H-tetrazole

Chemical Property of 5-(2-((4S,5R,6S)-6-((2R,3S)-3-methoxybutan-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)ethylsulfonyl)-1-phenyl-1H-tetrazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of 5-(2-((4S,5R,6S)-6-((2R,3S)-3-methoxybutan-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)ethylsulfonyl)-1-phenyl-1H-tetrazole

There total 7 articles about 5-(2-((4S,5R,6S)-6-((2R,3S)-3-methoxybutan-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)ethylsulfonyl)-1-phenyl-1H-tetrazole 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: 85.0%

C21H32N4O3S (1415654-87-3) → 5-(2-((4S,5R,6S)-6-((2R,3S)-3-methoxybutan-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)ethylsulfonyl)-1-phenyl-1H-tetrazole (1415654-67-9)

Guidance literature:

With ammonium molybdate; dihydrogen peroxide; In ethanol; water; at 0 - 20 ℃; for 16h;

DOI:10.1021/jo302205t

Reference yield:

C6H12O2 (955044-11-8) → 5-(2-((4S,5R,6S)-6-((2R,3S)-3-methoxybutan-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)ethylsulfonyl)-1-phenyl-1H-tetrazole (1415654-67-9)

Guidance literature:

Multi-step reaction with 14 steps

1.1: dichloromethane / 3 h / 20 °C / Inert atmosphere

2.1: triethylamine; sodium hydrogencarbonate; water / dichloromethane / 3 h / 20 °C / pH >7

3.1: triethylamine / dichloromethane / 0 - 20 °C

4.1: sodium iodide / acetone / 24 h / Reflux

4.2: 1 h / Reflux

5.1: pyridinium p-toluenesulfonate / dichloromethane / 10 h / 20 °C

6.1: lithium; naphthalene / tetrahydrofuran / 0.5 h / -10 °C

7.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0 °C / Inert atmosphere

8.1: tetrahydrofuran / 0 - 20 °C

9.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0 °C / Inert atmosphere

10.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 1 h / 0 °C / Inert atmosphere

11.1: sodium hydride / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

11.2: 5 h / 20 °C

12.1: ozone / dichloromethane; methanol / -78 °C / Inert atmosphere

12.2: -78 °C

13.1: tributylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere

14.1: ammonium molybdate; dihydrogen peroxide / ethanol; water / 16 h / 0 - 20 °C

With sodium tetrahydroborate; ammonium molybdate; naphthalene; tributylphosphine; cerium(III) chloride heptahydrate; di-isopropyl azodicarboxylate; water; dihydrogen peroxide; pyridinium p-toluenesulfonate; lithium; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; ozone; triethylamine; sodium iodide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetone; 1.1: |Prins-Kriewitz Hydroxyinethylation / 13.1: |Mitsunobu Displacement;

DOI:10.1021/jo302205t

Reference yield:

(4S,5R,6S)-4-allyl-6-((R)-1-(benzyloxy)propan-2-yl)-2,2,5-trimethyl-1,3-dioxane (1415654-80-6) → 5-(2-((4S,5R,6S)-6-((2R,3S)-3-methoxybutan-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)ethylsulfonyl)-1-phenyl-1H-tetrazole (1415654-67-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: lithium; naphthalene / tetrahydrofuran / 0.5 h / -10 °C

2.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0 °C / Inert atmosphere

3.1: tetrahydrofuran / 0 - 20 °C

4.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0 °C / Inert atmosphere

5.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 1 h / 0 °C / Inert atmosphere

6.1: sodium hydride / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

6.2: 5 h / 20 °C

7.1: ozone / dichloromethane; methanol / -78 °C / Inert atmosphere

7.2: -78 °C

8.1: tributylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere

9.1: ammonium molybdate; dihydrogen peroxide / ethanol; water / 16 h / 0 - 20 °C

With sodium tetrahydroborate; ammonium molybdate; naphthalene; tributylphosphine; cerium(III) chloride heptahydrate; di-isopropyl azodicarboxylate; dihydrogen peroxide; lithium; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; ozone; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; 8.1: |Mitsunobu Displacement;

DOI:10.1021/jo302205t

upstream raw materials:

C₆H₁₂O₂

(4S,5R,6S)-4-allyl-6-((R)-1-(benzyloxy)propan-2-yl)-2,2,5-trimethyl-1,3-dioxane

(S)-3-((4R,5R,6S)-6-allyl-2,2,5-trimethyl-1,3-dioxan-4-yl)-butan-2-one

(2S,3R)-3-((4S,5R,6S)-6-allyl-2,2,5-trimethyl-1,3-dioxan-4-yl)-butan-2-ol

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