(1S,2S,4R,8R,9R)-7-oxo-4-(toluene-4-sulfonyloxy)-10,11-dioxa-6-aza-tricyclo[6.2.1.0]undecane-9-carboxylic acid methyl ester

Base Information

• Chemical Name: (1S,2S,4R,8R,9R)-7-oxo-4-(toluene-4-sulfonyloxy)-10,11-dioxa-6-aza-tricyclo[6.2.1.0]undecane-9-carboxylic acid methyl ester
• CAS No.: 869649-42-3
• Molecular Formula: C₁₇H₁₉NO₈S
• Molecular Weight: 397.406
• Mol file: 869649-42-3.mol

Synonyms:

Chemical Property of (1S,2S,4R,8R,9R)-7-oxo-4-(toluene-4-sulfonyloxy)-10,11-dioxa-6-aza-tricyclo[6.2.1.0]undecane-9-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,4R,8R,9R)-7-oxo-4-(toluene-4-sulfonyloxy)-10,11-dioxa-6-aza-tricyclo[6.2.1.0]undecane-9-carboxylic acid methyl ester

There total 4 articles about (1S,2S,4R,8R,9R)-7-oxo-4-(toluene-4-sulfonyloxy)-10,11-dioxa-6-aza-tricyclo[6.2.1.0]undecane-9-carboxylic acid methyl 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: 46.0%

(1S,2S,4R,8R,9R)-4-hydroxy-7-oxo-10,11-dioxa-6-aza-tricyclo[6.2.1.0]undecane-9-carboxylic acid methyl ester (869648-72-6) + p-toluenesulfonyl chloride (98-59-9) → (1S,2S,4R,8R,9R)-7-oxo-4-(toluene-4-sulfonyloxy)-10,11-dioxa-6-aza-tricyclo[6.2.1.0]undecane-9-carboxylic acid methyl ester (869649-42-3)

Guidance literature:

In pyridine; at 20 ℃; for 12h;

DOI:10.1016/j.tetlet.2005.09.021

Reference yield:

(2S,4R)-4-benzyloxy-2-dimethoxymethyl-pyrrolidine (755729-83-0) → (1S,2S,4R,8R,9R)-7-oxo-4-(toluene-4-sulfonyloxy)-10,11-dioxa-6-aza-tricyclo[6.2.1.0]undecane-9-carboxylic acid methyl ester (869649-42-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 62 percent / PyBrOP; DIPEA / CH₂Cl₂ / 12 h / 20 °C

2: 67 percent / sulfuric acid; SiO₂; 4 Angstroem molecular sieves / toluene / 1 h / Heating

3: 27 percent / H₂ / Pd/C / ethanol / 72 h / 20 °C

4: 46 percent / pyridine / 12 h / 20 °C

With 4 A molecular sieve; sulfuric acid; hydrogen; silica gel; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; palladium on activated charcoal; In pyridine; ethanol; dichloromethane; toluene;

DOI:10.1016/j.tetlet.2005.09.021

Reference yield:

(1S,2S,4R,8R,9R)-4-benzyloxy-7-oxo-10,11-dioxa-6-aza-tricyclo[6.2.1.0]undecane-9-carboxylic acid methyl ester (869649-15-0) → (1S,2S,4R,8R,9R)-7-oxo-4-(toluene-4-sulfonyloxy)-10,11-dioxa-6-aza-tricyclo[6.2.1.0]undecane-9-carboxylic acid methyl ester (869649-42-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 27 percent / H₂ / Pd/C / ethanol / 72 h / 20 °C

2: 46 percent / pyridine / 12 h / 20 °C

With hydrogen; palladium on activated charcoal; In pyridine; ethanol;

DOI:10.1016/j.tetlet.2005.09.021

upstream raw materials:

(1S,2S,4R,8R,9R)-4-hydroxy-7-oxo-10,11-dioxa-6-aza-tricyclo[6.2.1.0]undecane-9-carboxylic acid methyl ester

p-toluenesulfonyl chloride

(2S,4R)-4-benzyloxy-2-dimethoxymethyl-pyrrolidine

(1S,2S,4R,8R,9R)-4-benzyloxy-7-oxo-10,11-dioxa-6-aza-tricyclo[6.2.1.0]undecane-9-carboxylic acid methyl ester