trifluoro-methanesulfonic acid 4-(tert-butyl-dimethyl-silanyloxy)-6-(3-{6-[2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-butyl]-5,6-dihydro-4H-pyran-2-yl}-3-methyl-but-1-enyl)-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: trifluoro-methanesulfonic acid 4-(tert-butyl-dimethyl-silanyloxy)-6-(3-{6-[2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-butyl]-5,6-dihydro-4H-pyran-2-yl}-3-methyl-but-1-enyl)-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 215876-21-4
• Molecular Formula: C₄₁H₆₉F₃O₉SSi₂
• Molecular Weight: 851.226
• Mol file: 215876-21-4.mol

Synonyms:trifluoro-methanesulfonic acid 4-(tert-butyl-dimethyl-silanyloxy)-6-(3-{6-[2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-butyl]-5,6-dihydro-4H-pyran-2-yl}-3-methyl-but-1-enyl)-tetrahydro-pyran-2-ylmethyl ester

Chemical Property of trifluoro-methanesulfonic acid 4-(tert-butyl-dimethyl-silanyloxy)-6-(3-{6-[2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-butyl]-5,6-dihydro-4H-pyran-2-yl}-3-methyl-but-1-enyl)-tetrahydro-pyran-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of trifluoro-methanesulfonic acid 4-(tert-butyl-dimethyl-silanyloxy)-6-(3-{6-[2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-butyl]-5,6-dihydro-4H-pyran-2-yl}-3-methyl-but-1-enyl)-tetrahydro-pyran-2-ylmethyl ester

There total 36 articles about trifluoro-methanesulfonic acid 4-(tert-butyl-dimethyl-silanyloxy)-6-(3-{6-[2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-butyl]-5,6-dihydro-4H-pyran-2-yl}-3-methyl-but-1-enyl)-tetrahydro-pyran-2-ylmethyl 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: 95.0%

trifluoromethylsulfonic anhydride (358-23-6) + [(2S,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-((E)-3-{(S)-6-[(2R,3R)-2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-butyl]-5,6-dihydro-4H-pyran-2-yl}-3-methyl-but-1-enyl)-tetrahydro-pyran-2-yl]-methanol (247146-85-6) → trifluoro-methanesulfonic acid 4-(tert-butyl-dimethyl-silanyloxy)-6-(3-{6-[2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-butyl]-5,6-dihydro-4H-pyran-2-yl}-3-methyl-but-1-enyl)-tetrahydro-pyran-2-ylmethyl ester (215876-21-4)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -10 ℃;

DOI:10.1021/ja990860j

Reference yield:

(2R,4S,6S)-2-Benzyloxymethyl-6-hydroxymethyl-tetrahydro-pyran-4-ol (215876-11-2) → trifluoro-methanesulfonic acid 4-(tert-butyl-dimethyl-silanyloxy)-6-(3-{6-[2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-butyl]-5,6-dihydro-4H-pyran-2-yl}-3-methyl-but-1-enyl)-tetrahydro-pyran-2-ylmethyl ester (215876-21-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: imidazole; DMAP / CH₂Cl₂

2.1: H₂; AcOH / 10 percent Pd/C / ethyl acetate / 760 Torr

3.1: 85 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - -50 °C

4.1: n-BuLi / tetrahydrofuran / -78 °C

4.2: tetrahydrofuran / -78 - -50 °C

5.1: DMAP / CH₂Cl₂

6.1: 64 percent / Mg; HgCl₂; EtOH

7.1: 75 percent / TBAF / tetrahydrofuran / -15 °C

8.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / -10 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; n-butyllithium; oxalyl dichloride; ethanol; tetrabutyl ammonium fluoride; hydrogen; magnesium; acetic acid; dimethyl sulfoxide; triethylamine; mercury dichloride; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; 1.1: silylation / 2.1: Hydrogenolysis / 3.1: Oxidation / 4.1: Metallation / 4.2: Substitution / 5.1: Acetylation / 6.1: Deacetylation / 7.1: desilylation / 8.1: Esterification;

DOI:10.1021/ja990860j

Reference yield:

2-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran (247146-46-9) → trifluoro-methanesulfonic acid 4-(tert-butyl-dimethyl-silanyloxy)-6-(3-{6-[2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-butyl]-5,6-dihydro-4H-pyran-2-yl}-3-methyl-but-1-enyl)-tetrahydro-pyran-2-ylmethyl ester (215876-21-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: H₂; AcOH / 10 percent Pd/C / ethyl acetate / 760 Torr

2.1: 85 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - -50 °C

3.1: n-BuLi / tetrahydrofuran / -78 °C

3.2: tetrahydrofuran / -78 - -50 °C

4.1: DMAP / CH₂Cl₂

5.1: 64 percent / Mg; HgCl₂; EtOH

6.1: 75 percent / TBAF / tetrahydrofuran / -15 °C

7.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / -10 °C

With 2,6-dimethylpyridine; dmap; n-butyllithium; oxalyl dichloride; ethanol; tetrabutyl ammonium fluoride; hydrogen; magnesium; acetic acid; dimethyl sulfoxide; triethylamine; mercury dichloride; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; 1.1: Hydrogenolysis / 2.1: Oxidation / 3.1: Metallation / 3.2: Substitution / 4.1: Acetylation / 5.1: Deacetylation / 6.1: desilylation / 7.1: Esterification;

DOI:10.1021/ja990860j

upstream raw materials:

trifluoromethylsulfonic anhydride

[(2S,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-((E)-3-{(S)-6-[(2R,3R)-2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-butyl]-5,6-dihydro-4H-pyran-2-yl}-3-methyl-but-1-enyl)-tetrahydro-pyran-2-yl]-methanol

2-Phenylthiomethyl-2-methyl-1-propanol

3-hydroxy-2,2-dimethylpropyl 4-methylbenzenesulfonate

Downstream raw materials:

C₇₇H₁₂₉NO₁₂Si₄

C₇₁H₁₁₅NO₁₂Si₃