(1R,5S,8S,9S)-methanesulfonic acid 2-benzyl-9-hydroxy-6,6-dimethyl-3,7-dioxa-2-azabicyclo[3.3.1]non-8-ylmethyl ester

Base Information

• Chemical Name: (1R,5S,8S,9S)-methanesulfonic acid 2-benzyl-9-hydroxy-6,6-dimethyl-3,7-dioxa-2-azabicyclo[3.3.1]non-8-ylmethyl ester
• CAS No.: 870461-31-7
• Molecular Formula: C₁₇H₂₅NO₆S
• Molecular Weight: 371.455
• Mol file: 870461-31-7.mol

Synonyms:(1R,5S,8S,9S)-methanesulfonic acid 2-benzyl-9-hydroxy-6,6-dimethyl-3,7-dioxa-2-azabicyclo[3.3.1]non-8-ylmethyl ester

Chemical Property of (1R,5S,8S,9S)-methanesulfonic acid 2-benzyl-9-hydroxy-6,6-dimethyl-3,7-dioxa-2-azabicyclo[3.3.1]non-8-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,5S,8S,9S)-methanesulfonic acid 2-benzyl-9-hydroxy-6,6-dimethyl-3,7-dioxa-2-azabicyclo[3.3.1]non-8-ylmethyl ester

There total 2 articles about (1R,5S,8S,9S)-methanesulfonic acid 2-benzyl-9-hydroxy-6,6-dimethyl-3,7-dioxa-2-azabicyclo[3.3.1]non-8-ylmethyl ester 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:

(1S,5R,8S)-2-benzyl-8-(hydroxymethyl)-6,6-dimethyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-one (444307-98-6) → (1R,5S,8S,9S)-methanesulfonic acid 2-benzyl-9-hydroxy-6,6-dimethyl-3,7-dioxa-2-azabicyclo[3.3.1]non-8-ylmethyl ester (870461-31-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / triethylamine / CH₂Cl₂ / 4 h / 0 °C

2: 85 percent / NaBH₄ / ethanol / 3 h / 20 °C

With sodium tetrahydroborate; triethylamine; In ethanol; dichloromethane;

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) → (1R,5S,8S,9S)-methanesulfonic acid 2-benzyl-9-hydroxy-6,6-dimethyl-3,7-dioxa-2-azabicyclo[3.3.1]non-8-ylmethyl ester (870461-31-7)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 85 percent / NaBH₄ / ethanol / 3 h / 20 °C

With sodium tetrahydroborate; tin(IV) chloride; triethylamine; In ethanol; dichloromethane; acetonitrile;

DOI:10.1002/anie.200501127

Reference yield: 81.0%

(1R,5S,8S,9S)-methanesulfonic acid 2-benzyl-9-hydroxy-6,6-dimethyl-3,7-dioxa-2-azabicyclo[3.3.1]non-8-ylmethyl ester (870461-31-7) → (1R,5S,8R,9S)-8-azidomethyl-2-benzyl-6,6-dimethyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-ol (870461-32-8)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 80 ℃; for 6h; Inert atmosphere;

DOI:10.1002/chem.200900996

upstream raw materials:

(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