Benzoic acid (2R,4S,6S)-2-benzyloxymethyl-6-[(4S,6S)-6-[(R)-3-tert-butylcarbamoyl-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(4-methoxy-benzyloxy)-3,3-dimethyl-tetrahydro-pyran-(2Z)-ylidenemethyl]-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,4S,6S)-2-benzyloxymethyl-6-[(4S,6S)-6-[(R)-3-tert-butylcarbamoyl-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(4-methoxy-benzyloxy)-3,3-dimethyl-tetrahydro-pyran-(2Z)-ylidenemethyl]-tetrahydro-pyran-4-yl ester
• CAS No.: 247146-33-4
• Molecular Formula: C₅₀H₇₁NO₉Si
• Molecular Weight: 858.201
• Mol file: 247146-33-4.mol

Synonyms:Benzoic acid (2R,4S,6S)-2-benzyloxymethyl-6-[(4S,6S)-6-[(R)-3-tert-butylcarbamoyl-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(4-methoxy-benzyloxy)-3,3-dimethyl-tetrahydro-pyran-(2Z)-ylidenemethyl]-tetrahydro-pyran-4-yl ester

Chemical Property of Benzoic acid (2R,4S,6S)-2-benzyloxymethyl-6-[(4S,6S)-6-[(R)-3-tert-butylcarbamoyl-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(4-methoxy-benzyloxy)-3,3-dimethyl-tetrahydro-pyran-(2Z)-ylidenemethyl]-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2R,4S,6S)-2-benzyloxymethyl-6-[(4S,6S)-6-[(R)-3-tert-butylcarbamoyl-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(4-methoxy-benzyloxy)-3,3-dimethyl-tetrahydro-pyran-(2Z)-ylidenemethyl]-tetrahydro-pyran-4-yl ester

There total 24 articles about Benzoic acid (2R,4S,6S)-2-benzyloxymethyl-6-[(4S,6S)-6-[(R)-3-tert-butylcarbamoyl-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(4-methoxy-benzyloxy)-3,3-dimethyl-tetrahydro-pyran-(2Z)-ylidenemethyl]-tetrahydro-pyran-4-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: 45.0%

Benzoic acid (2R,4R,6S)-2-benzyloxymethyl-6-trifluoromethanesulfonyloxymethyl-tetrahydro-pyran-4-yl ester (247146-32-3) + 4-[6-benzenesulfonyl-4-(4-methoxy-benzyloxy)-5,5-dimethyl-tetrahydro-pyran-2-yl]-N-tert-butyl-3-(tert-butyl-dimethyl-silanyloxy)-butyramide (247146-60-7) → Benzoic acid (2R,4S,6S)-2-benzyloxymethyl-6-[(4S,6S)-6-[(R)-3-tert-butylcarbamoyl-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(4-methoxy-benzyloxy)-3,3-dimethyl-tetrahydro-pyran-(2Z)-ylidenemethyl]-tetrahydro-pyran-4-yl ester (247146-33-4)

Guidance literature:

4-[6-benzenesulfonyl-4-(4-methoxy-benzyloxy)-5,5-dimethyl-tetrahydro-pyran-2-yl]-N-tert-butyl-3-(tert-butyl-dimethyl-silanyloxy)-butyramide; In tetrahydrofuran; at -78 ℃;

Benzoic acid (2R,4R,6S)-2-benzyloxymethyl-6-trifluoromethanesulfonyloxymethyl-tetrahydro-pyran-4-yl ester; With N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; at -78 - 23 ℃;

DOI:10.1021/ja990860j

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → Benzoic acid (2R,4S,6S)-2-benzyloxymethyl-6-[(4S,6S)-6-[(R)-3-tert-butylcarbamoyl-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(4-methoxy-benzyloxy)-3,3-dimethyl-tetrahydro-pyran-(2Z)-ylidenemethyl]-tetrahydro-pyran-4-yl ester (247146-33-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 64 percent / 2,6-lutidine / CH₂Cl₂ / -10 °C

2.1: 96 percent / Me₃Al / tetrahydrofuran / 16 h / 20 °C

3.1: O₃ / CH₂Cl₂; methanol / -78 °C

3.2: Me₂S / methanol; CH₂Cl₂

4.1: pyridine / 48 h / 23 °C

5.1: ZnI₂; n-Bu₄NI / CH₂Cl₂

6.1: m-CPBA; NaHCO₃ / ethyl acetate

7.1: tetrahydrofuran / -78 °C

7.2: 45 percent / HMPA / tetrahydrofuran / -78 - 23 °C

With pyridine; 2,6-dimethylpyridine; trimethylaluminum; tetra-(n-butyl)ammonium iodide; sodium hydrogencarbonate; ozone; 3-chloro-benzenecarboperoxoic acid; zinc(II) iodide; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; 1.1: silylation / 2.1: Ring cleavage / 3.1: ozonolysis / 3.2: Reduction / 4.1: Acetylation / 5.1: Substitution / 6.1: Oxidation / 7.1: Metallation / 7.2: Substitution;

DOI:10.1021/ja990860j

Reference yield:

benzoic acid anhydride (93-97-0) → Benzoic acid (2R,4S,6S)-2-benzyloxymethyl-6-[(4S,6S)-6-[(R)-3-tert-butylcarbamoyl-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(4-methoxy-benzyloxy)-3,3-dimethyl-tetrahydro-pyran-(2Z)-ylidenemethyl]-tetrahydro-pyran-4-yl ester (247146-33-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: DMAP

2.1: TBAF / tetrahydrofuran / 0 °C

3.1: 89 percent / 2,6-lutidine / -10 °C

4.1: tetrahydrofuran / -78 °C

4.2: 45 percent / HMPA / tetrahydrofuran / -78 - 23 °C

With 2,6-dimethylpyridine; dmap; tetrabutyl ammonium fluoride; In tetrahydrofuran; 1.1: Acylation / 2.1: desilylation / 3.1: Esterification / 4.1: Metallation / 4.2: Substitution;

DOI:10.1021/ja990860j

upstream raw materials:

Benzoic acid (2R,4R,6S)-2-benzyloxymethyl-6-trifluoromethanesulfonyloxymethyl-tetrahydro-pyran-4-yl ester

4-[6-benzenesulfonyl-4-(4-methoxy-benzyloxy)-5,5-dimethyl-tetrahydro-pyran-2-yl]-N-tert-butyl-3-(tert-butyl-dimethyl-silanyloxy)-butyramide

t-butyldimethylsiyl triflate

benzoic acid anhydride