Acetic acid (2S,4aR,6R,7R,8S,8aS)-7-acetoxy-6-[3-(tert-butyl-dimethyl-silanyloxy)-3-cyano-propylsulfanyl]-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Base Information

• Chemical Name: Acetic acid (2S,4aR,6R,7R,8S,8aS)-7-acetoxy-6-[3-(tert-butyl-dimethyl-silanyloxy)-3-cyano-propylsulfanyl]-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester
• CAS No.: 870192-83-9
• Molecular Formula: C₂₈H₄₁NO₉SSi
• Molecular Weight: 595.786

Synonyms:Acetic acid (2S,4aR,6R,7R,8S,8aS)-7-acetoxy-6-[3-(tert-butyl-dimethyl-silanyloxy)-3-cyano-propylsulfanyl]-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Chemical Property of Acetic acid (2S,4aR,6R,7R,8S,8aS)-7-acetoxy-6-[3-(tert-butyl-dimethyl-silanyloxy)-3-cyano-propylsulfanyl]-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of Acetic acid (2S,4aR,6R,7R,8S,8aS)-7-acetoxy-6-[3-(tert-butyl-dimethyl-silanyloxy)-3-cyano-propylsulfanyl]-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

There total 8 articles about Acetic acid (2S,4aR,6R,7R,8S,8aS)-7-acetoxy-6-[3-(tert-butyl-dimethyl-silanyloxy)-3-cyano-propylsulfanyl]-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl 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: 93.0%

2-(tert-Butyl-dimethyl-silanyloxy)-4-[(2S,4aR,6R,7R,8R,8aR)-7,8-dihydroxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-ylsulfanyl]-butyronitrile (874634-84-1) + acetic anhydride (108-24-7) → Acetic acid (2S,4aR,6R,7R,8S,8aS)-7-acetoxy-6-[3-(tert-butyl-dimethyl-silanyloxy)-3-cyano-propylsulfanyl]-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (870192-83-9)

Guidance literature:

With pyridine;

DOI:10.1016/j.bmcl.2005.08.019

Reference yield:

2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl chloride (572-10-1,4451-35-8,4451-36-9,14227-52-2,14227-87-3,14227-88-4,14257-40-0,17081-03-7,19186-60-8,57237-01-1,65982-17-4,65982-18-5,65982-19-6,66966-08-3,144299-57-0) → Acetic acid (2S,4aR,6R,7R,8S,8aS)-7-acetoxy-6-[3-(tert-butyl-dimethyl-silanyloxy)-3-cyano-propylsulfanyl]-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (870192-83-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 50 °C

2: 89 percent / NaOMe / methanol / -25 °C

3: dimethylformamide

4: acetonitrile

5: NaOMe / methanol

6: CSA / dimethylformamide

7: 93 percent / pyridine

With pyridine; camphor-10-sulfonic acid; sodium methylate; In methanol; N,N-dimethyl-formamide; acetonitrile; 3: Michael addition;

DOI:10.1016/j.bmcl.2005.08.019

Reference yield:

2,3,4,6-tetra-O-acetyl-1-thio-D-galactopyranose (380224-05-5) → Acetic acid (2S,4aR,6R,7R,8S,8aS)-7-acetoxy-6-[3-(tert-butyl-dimethyl-silanyloxy)-3-cyano-propylsulfanyl]-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (870192-83-9)

Guidance literature:

Multi-step reaction with 5 steps

1: dimethylformamide

2: acetonitrile

3: NaOMe / methanol

4: CSA / dimethylformamide

5: 93 percent / pyridine

With pyridine; camphor-10-sulfonic acid; sodium methylate; In methanol; N,N-dimethyl-formamide; acetonitrile; 1: Michael addition;

DOI:10.1016/j.bmcl.2005.08.019

upstream raw materials:

2-(tert-Butyl-dimethyl-silanyloxy)-4-[(2S,4aR,6R,7R,8R,8aR)-7,8-dihydroxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-ylsulfanyl]-butyronitrile

acetic anhydride

2,3,4,6-tetra-O-acetyl-1-thio-D-galactopyranose

Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[3-(tert-butyl-dimethyl-silanyloxy)-3-cyano-propylsulfanyl]-tetrahydro-pyran-4-yl ester

Downstream raw materials:

C₇₂H₈₀O₂₄S

C₅₄H₆₆O₂₅S

C₅₃H₆₆O₂₄S

(2R,3R,4R,5R,6S)-4,5-Diacetoxy-3-[(2S,4aR,6R,7R,8S,8aS)-7,8-diacetoxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-ylsulfanyl]-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

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