Methanesulfonic acid (S)-2-{(4R,5R)-5-[(S)-2-methanesulfonyloxy-1-(toluene-4-sulfonylamino)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-(toluene-4-sulfonylamino)-ethyl ester

Base Information

• Chemical Name: Methanesulfonic acid (S)-2-{(4R,5R)-5-[(S)-2-methanesulfonyloxy-1-(toluene-4-sulfonylamino)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-(toluene-4-sulfonylamino)-ethyl ester
• CAS No.: 914982-51-7
• Molecular Formula: C₂₅H₃₆N₂O₁₂S₄
• Molecular Weight: 684.831
• Mol file: 914982-51-7.mol

Synonyms:Methanesulfonic acid (S)-2-{(4R,5R)-5-[(S)-2-methanesulfonyloxy-1-(toluene-4-sulfonylamino)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-(toluene-4-sulfonylamino)-ethyl ester

Chemical Property of Methanesulfonic acid (S)-2-{(4R,5R)-5-[(S)-2-methanesulfonyloxy-1-(toluene-4-sulfonylamino)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-(toluene-4-sulfonylamino)-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methanesulfonic acid (S)-2-{(4R,5R)-5-[(S)-2-methanesulfonyloxy-1-(toluene-4-sulfonylamino)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-(toluene-4-sulfonylamino)-ethyl ester

There total 9 articles about Methanesulfonic acid (S)-2-{(4R,5R)-5-[(S)-2-methanesulfonyloxy-1-(toluene-4-sulfonylamino)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-(toluene-4-sulfonylamino)-ethyl 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: 92.0%

C23H32N2O8S2 (914982-50-6) + methanesulfonyl chloride (124-63-0) → Methanesulfonic acid (S)-2-{(4R,5R)-5-[(S)-2-methanesulfonyloxy-1-(toluene-4-sulfonylamino)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-(toluene-4-sulfonylamino)-ethyl ester (914982-51-7)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1016/j.tet.2006.08.035

Reference yield:

(S)-2-benzyloxy-1-((4R,5R)-5-((S)-2-benzyloxy-1-(tosylamino)ethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-N-tosylethanamine (914982-45-9) → Methanesulfonic acid (S)-2-{(4R,5R)-5-[(S)-2-methanesulfonyloxy-1-(toluene-4-sulfonylamino)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-(toluene-4-sulfonylamino)-ethyl ester (914982-51-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / hydrogen / Pd/C / methanol / 12 h / 20 °C / atmospheric pressure

2: 92 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

With hydrogen; triethylamine; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1016/j.tet.2006.08.035

Reference yield:

1,3:4,6-di-O-benzylidene-D-mannitol (61490-28-6) → Methanesulfonic acid (S)-2-{(4R,5R)-5-[(S)-2-methanesulfonyloxy-1-(toluene-4-sulfonylamino)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-(toluene-4-sulfonylamino)-ethyl ester (914982-51-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 82 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

2: 78 percent / BF₃*Et₂O; Et₃SiH / CH₂Cl₂ / 1 h

3: 80 percent / pTSA / acetone / 5 h / 20 °C

4: 91 percent / sodium azide / dimethylformamide / 24 h / 110 °C

5: 95 percent / hydrogen / Lindlar's catalyst / methanol / 4 h / 28 °C / 760 Torr

6: 86 percent / pyridine / 3 h / 0 - 20 °C

7: 90 percent / hydrogen / Pd/C / methanol / 12 h / 20 °C / atmospheric pressure

8: 92 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

With pyridine; triethylsilane; sodium azide; boron trifluoride diethyl etherate; hydrogen; toluene-4-sulfonic acid; triethylamine; palladium on activated charcoal; Lindlar's catalyst; In methanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1016/j.tet.2006.08.035

upstream raw materials:

C₂₃H₃₂N₂O₈S₂

methanesulfonyl chloride

(S)-2-benzyloxy-1-((4R,5R)-5-((S)-2-benzyloxy-1-(tosylamino)ethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-N-tosylethanamine

1,3:4,6-di-O-benzylidene-D-mannitol