Acetic acid (2S,4R)-2,4-bis-(tert-butyl-diphenyl-silanyloxy)-8-(4-methoxy-benzyloxy)-1-phenylsulfanyl-oct-6-ynyl ester

Base Information

• Chemical Name: Acetic acid (2S,4R)-2,4-bis-(tert-butyl-diphenyl-silanyloxy)-8-(4-methoxy-benzyloxy)-1-phenylsulfanyl-oct-6-ynyl ester
• CAS No.: 249570-30-7
• Molecular Formula: C₅₆H₆₄O₆SSi₂
• Molecular Weight: 921.358
• Mol file: 249570-30-7.mol

Synonyms:

Chemical Property of Acetic acid (2S,4R)-2,4-bis-(tert-butyl-diphenyl-silanyloxy)-8-(4-methoxy-benzyloxy)-1-phenylsulfanyl-oct-6-ynyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2S,4R)-2,4-bis-(tert-butyl-diphenyl-silanyloxy)-8-(4-methoxy-benzyloxy)-1-phenylsulfanyl-oct-6-ynyl ester

There total 6 articles about Acetic acid (2S,4R)-2,4-bis-(tert-butyl-diphenyl-silanyloxy)-8-(4-methoxy-benzyloxy)-1-phenylsulfanyl-oct-6-ynyl 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: 74.0%

acetic anhydride (108-24-7) + 1-[(5R,7S)-8-Benzenesulfinyl-5,7-bis-(tert-butyl-diphenyl-silanyloxy)-oct-2-ynyloxymethyl]-4-methoxy-benzene (249570-28-3) → Acetic acid (2S,4R)-2,4-bis-(tert-butyl-diphenyl-silanyloxy)-8-(4-methoxy-benzyloxy)-1-phenylsulfanyl-oct-6-ynyl ester (249570-30-7)

Guidance literature:

With sodium acetate; for 11h; Heating;

DOI:10.1055/s-1999-2842

Reference yield:

(2S,4S)-1,2:4,5-dianhydro-3-deoxypentitol (109905-51-3) → Acetic acid (2S,4R)-2,4-bis-(tert-butyl-diphenyl-silanyloxy)-8-(4-methoxy-benzyloxy)-1-phenylsulfanyl-oct-6-ynyl ester (249570-30-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 53 percent / n-BuLi; BF₃*Et₂O / tetrahydrofuran / 1.5 h / -78 °C

2: NaOH / dioxane / 3 h / Heating

3: imidazole; DMAP / CH₂Cl₂; diethyl ether / 0 - 20 °C

4: 91 percent / mCPBA / CH₂Cl₂ / 7 h / 20 °C

5: 74 percent / NaOAc / 11 h / Heating

With 1H-imidazole; dmap; sodium hydroxide; n-butyllithium; boron trifluoride diethyl etherate; sodium acetate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; 1: Substitution / 2: Substitution / 3: Substitution / 4: Oxidation / 5: Rearrangement;

DOI:10.1055/s-1999-2842

Reference yield:

3-(4-methoxybenzyloxy)propyne (4039-83-2) → Acetic acid (2S,4R)-2,4-bis-(tert-butyl-diphenyl-silanyloxy)-8-(4-methoxy-benzyloxy)-1-phenylsulfanyl-oct-6-ynyl ester (249570-30-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 53 percent / n-BuLi; BF₃*Et₂O / tetrahydrofuran / 1.5 h / -78 °C

2: NaOH / dioxane / 3 h / Heating

3: imidazole; DMAP / CH₂Cl₂; diethyl ether / 0 - 20 °C

4: 91 percent / mCPBA / CH₂Cl₂ / 7 h / 20 °C

5: 74 percent / NaOAc / 11 h / Heating

With 1H-imidazole; dmap; sodium hydroxide; n-butyllithium; boron trifluoride diethyl etherate; sodium acetate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; 1: Substitution / 2: Substitution / 3: Substitution / 4: Oxidation / 5: Rearrangement;

DOI:10.1055/s-1999-2842

upstream raw materials:

acetic anhydride

1-[(5R,7S)-8-Benzenesulfinyl-5,7-bis-(tert-butyl-diphenyl-silanyloxy)-oct-2-ynyloxymethyl]-4-methoxy-benzene

(2S,4S)-1,2:4,5-dianhydro-3-deoxypentitol

3-(4-methoxybenzyloxy)propyne

Downstream raw materials:

1-[(5R,7S)-5,7-Bis-(tert-butyl-diphenyl-silanyloxy)-non-8-en-2-ynyloxymethyl]-4-methoxy-benzene