(2S,3S)-4-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-2-methyl-butyric acid (1S,2R)-2-[benzyl-(2,4,6-trimethyl-benzenesulfonyl)-amino]-1-phenyl-propyl ester

Base Information

• Chemical Name: (2S,3S)-4-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-2-methyl-butyric acid (1S,2R)-2-[benzyl-(2,4,6-trimethyl-benzenesulfonyl)-amino]-1-phenyl-propyl ester
• CAS No.: 202526-12-3
• Molecular Formula: C₃₅H₄₅NO₇S
• Molecular Weight: 623.811
• Mol file: 202526-12-3.mol

Synonyms:

Chemical Property of (2S,3S)-4-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-2-methyl-butyric acid (1S,2R)-2-[benzyl-(2,4,6-trimethyl-benzenesulfonyl)-amino]-1-phenyl-propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-4-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-2-methyl-butyric acid (1S,2R)-2-[benzyl-(2,4,6-trimethyl-benzenesulfonyl)-amino]-1-phenyl-propyl ester

There total 1 articles about (2S,3S)-4-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-2-methyl-butyric acid (1S,2R)-2-[benzyl-(2,4,6-trimethyl-benzenesulfonyl)-amino]-1-phenyl-propyl 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:

2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acetaldehyde (32233-44-6) + C40H54BNO4S → (2R,3R)-4-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-2-methyl-butyric acid (1S,2R)-2-[benzyl-(2,4,6-trimethyl-benzenesulfonyl)-amino]-1-phenyl-propyl ester + (2S,3S)-4-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-2-methyl-butyric acid (1S,2R)-2-[benzyl-(2,4,6-trimethyl-benzenesulfonyl)-amino]-1-phenyl-propyl ester (202526-12-3)

Guidance literature:

In dichloromethane; at -78 - 0 ℃; Yield given. Yields of byproduct given;

DOI:10.1021/jo971863m

Reference yield:

(2S,3S)-4-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-2-methyl-butyric acid (1S,2R)-2-[benzyl-(2,4,6-trimethyl-benzenesulfonyl)-amino]-1-phenyl-propyl ester (202526-12-3) → (2S,3S)-3-Benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-butyraldehyde (202526-31-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 60 percent / LAH / tetrahydrofuran / 0 °C

2: 83 percent / Et₃N, DMAP / CH₂Cl₂ / 25 °C

3: 85 percent / NaH / dimethylformamide / 25 °C

4: 94 percent / TBAF / tetrahydrofuran / 25 °C

5: Swern / -78 °C

With dmap; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo971863m

Reference yield:

(2S,3S)-4-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-2-methyl-butyric acid (1S,2R)-2-[benzyl-(2,4,6-trimethyl-benzenesulfonyl)-amino]-1-phenyl-propyl ester (202526-12-3) → (3S,4S,6S)-4-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-ol (202526-34-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 60 percent / LAH / tetrahydrofuran / 0 °C

2: 83 percent / Et₃N, DMAP / CH₂Cl₂ / 25 °C

3: 85 percent / NaH / dimethylformamide / 25 °C

4: 94 percent / TBAF / tetrahydrofuran / 25 °C

5: Swern / -78 °C

6: 1 N HCl / tetrahydrofuran / 25 °C

7: 95 percent / Et₃N, DMAP / CH₂Cl₂ / 25 °C

With hydrogenchloride; dmap; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo971863m

upstream raw materials:

2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acetaldehyde

Downstream raw materials:

(3S,4S,6S)-4-Benzyloxy-6-hydroxymethyl-3-methyl-tetrahydro-pyran-2-ol

(2R,3S)-3-Benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-butan-1-ol

(2S,3S)-3-Benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-butyraldehyde

(3S,4S,6S)-4-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-tetrahydro-pyran-2-ol