(3aR,6S,7R,7aR)-7-Hydroxy-2,2,6-trimethyl-5-(toluene-4-sulfonyl)-hexahydro-[1,3]dioxolo[4,5-c]pyridine-6-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (3aR,6S,7R,7aR)-7-Hydroxy-2,2,6-trimethyl-5-(toluene-4-sulfonyl)-hexahydro-[1,3]dioxolo[4,5-c]pyridine-6-carboxylic acid tert-butyl ester
• CAS No.: 616234-23-2
• Molecular Formula: C₂₁H₃₁NO₇S
• Molecular Weight: 441.546
• Mol file: 616234-23-2.mol

Synonyms:(3aR,6S,7R,7aR)-7-Hydroxy-2,2,6-trimethyl-5-(toluene-4-sulfonyl)-hexahydro-[1,3]dioxolo[4,5-c]pyridine-6-carboxylic acid tert-butyl ester

Chemical Property of (3aR,6S,7R,7aR)-7-Hydroxy-2,2,6-trimethyl-5-(toluene-4-sulfonyl)-hexahydro-[1,3]dioxolo[4,5-c]pyridine-6-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,6S,7R,7aR)-7-Hydroxy-2,2,6-trimethyl-5-(toluene-4-sulfonyl)-hexahydro-[1,3]dioxolo[4,5-c]pyridine-6-carboxylic acid tert-butyl ester

There total 4 articles about (3aR,6S,7R,7aR)-7-Hydroxy-2,2,6-trimethyl-5-(toluene-4-sulfonyl)-hexahydro-[1,3]dioxolo[4,5-c]pyridine-6-carboxylic acid tert-butyl 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: 72.0%

(2S,3R)-3-Hydroxy-3-((4R,5R)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-2-(toluene-4-sulfonylamino)-propionic acid tert-butyl ester (616234-22-1) → (3aR,6S,7R,7aR)-7-Hydroxy-2,2,6-trimethyl-5-(toluene-4-sulfonyl)-hexahydro-[1,3]dioxolo[4,5-c]pyridine-6-carboxylic acid tert-butyl ester (616234-23-2)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20 ℃;

DOI:10.1002/ejoc.200300079

Reference yield:

4-O-benzyl-2,3-O-isopropylidene-D-threose (81801-09-4) → (3aR,6S,7R,7aR)-7-Hydroxy-2,2,6-trimethyl-5-(toluene-4-sulfonyl)-hexahydro-[1,3]dioxolo[4,5-c]pyridine-6-carboxylic acid tert-butyl ester (616234-23-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 62 percent / tetrahydrofuran / -78 °C

2: 100 percent / hydrogen / Pd/C / methanol / 20 °C / 2250.18 Torr

3: 72 percent / DEAD; PPh₃ / tetrahydrofuran / 20 °C

With hydrogen; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; 1: aldol reaction / 3: Mitsunobu cyclization;

DOI:10.1002/ejoc.200300079

Reference yield:

(2S,3R)-3-((4R,5R)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-2-methyl-2-(toluene-4-sulfonylamino)-propionic acid tert-butyl ester → (3aR,6S,7R,7aR)-7-Hydroxy-2,2,6-trimethyl-5-(toluene-4-sulfonyl)-hexahydro-[1,3]dioxolo[4,5-c]pyridine-6-carboxylic acid tert-butyl ester (616234-23-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / hydrogen / Pd/C / methanol / 20 °C / 2250.18 Torr

2: 72 percent / DEAD; PPh₃ / tetrahydrofuran / 20 °C

With hydrogen; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; 2: Mitsunobu cyclization;

DOI:10.1002/ejoc.200300079

upstream raw materials:

(2S,3R)-3-Hydroxy-3-((4R,5R)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-2-(toluene-4-sulfonylamino)-propionic acid tert-butyl ester

4-O-benzyl-2,3-O-isopropylidene-D-threose

Downstream raw materials:

tert-butyl (2S,3R,4S,5R)-3,4,5-trihydroxy-2-methyl-1-(p-toluenesulfonyl)piperidine-2-carboxylate

tert-butyl (2S,3R,4S,5R)-3,4,5-tris(benzyloxy)-2-methyl-1-(p-toluenesulfonyl)piperidine-2-carboxylate

(2R,3R,4S,5R)-3,4,5-tris(benzyloxy)-1-[2'-(diethoxyphosphoryl)acetyl]-2-hydroxymethyl-2-methylpiperidine

(2R,3R,4S,5R)-3,4,5-tris(benzyloxy)-2-hydroxymethyl-2-methyl-1-(p-toluenesulfonyl)piperidine