3,7-Dioxa-2-azabicyclo[3.3.1]nonan-9-one, 6,6-dimethyl-8-[[(methylsulfonyl)oxy]methyl]-2-(phenylmethyl)-, (1S,5R,8S)-

Base Information

• Chemical Name: 3,7-Dioxa-2-azabicyclo[3.3.1]nonan-9-one, 6,6-dimethyl-8-[[(methylsulfonyl)oxy]methyl]-2-(phenylmethyl)-, (1S,5R,8S)-
• CAS No.: 870461-34-0
• Molecular Formula: C17H23NO6S
• Molecular Weight: 369.439
• Mol file: 870461-34-0.mol

Synonyms:

Chemical Property of 3,7-Dioxa-2-azabicyclo[3.3.1]nonan-9-one, 6,6-dimethyl-8-[[(methylsulfonyl)oxy]methyl]-2-(phenylmethyl)-, (1S,5R,8S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,7-Dioxa-2-azabicyclo[3.3.1]nonan-9-one, 6,6-dimethyl-8-[[(methylsulfonyl)oxy]methyl]-2-(phenylmethyl)-, (1S,5R,8S)-

There total 2 articles about 3,7-Dioxa-2-azabicyclo[3.3.1]nonan-9-one, 6,6-dimethyl-8-[[(methylsulfonyl)oxy]methyl]-2-(phenylmethyl)-, (1S,5R,8S)- 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: 100.0%

methanesulfonyl chloride (124-63-0) + (1S,5R,8S)-2-benzyl-8-(hydroxymethyl)-6,6-dimethyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-one (444307-98-6) → (1S,5R,8S)-methanesulfonic acid (2-benzyl-6,6-dimethyl-9-oxo-3,7-dioxa-2-azabicyclo[3.3.1]non-8-yl)methyl ester (870461-34-0)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 4h;

DOI:10.1002/anie.200501127

Reference yield:

(3S,4'S)-2-benzyl-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4-[2-(trimethylsilyl)ethoxy]-3,6-dihydro-2H-1,2-oxazine (444307-95-3) → (1S,5R,8S)-methanesulfonic acid (2-benzyl-6,6-dimethyl-9-oxo-3,7-dioxa-2-azabicyclo[3.3.1]non-8-yl)methyl ester (870461-34-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / SnCl₄ / acetonitrile / 6 h / -30 - 20 °C

2: 100 percent / triethylamine / CH₂Cl₂ / 4 h / 0 °C

With tin(IV) chloride; triethylamine; In dichloromethane; acetonitrile;

DOI:10.1002/anie.200501127

Reference yield: 71.0%

pyrrolidine (123-75-1) + (1S,5R,8S)-methanesulfonic acid (2-benzyl-6,6-dimethyl-9-oxo-3,7-dioxa-2-azabicyclo[3.3.1]non-8-yl)methyl ester (870461-34-0) → (1S,5R,8R)-2-benzyl-6,6-dimethyl-8-(pyrrolidin-1-ylmethyl)-3,7-dioxa-2-aza-bicyclo[3.3.1]nonan-9-one

Guidance literature:

In 1,4-dioxane; at 100 ℃; for 17h; Sealed tube;

DOI:10.1080/00397911.2018.1468465

upstream raw materials:

methanesulfonyl chloride

(1S,5R,8S)-2-benzyl-8-(hydroxymethyl)-6,6-dimethyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-one

(3S,4'S)-2-benzyl-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4-[2-(trimethylsilyl)ethoxy]-3,6-dihydro-2H-1,2-oxazine

Downstream raw materials:

(1R,5S,8R,9S)-8-azidomethyl-2-benzyl-6,6-dimethyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-ol