2,2-Dimethyl-propionic acid (2R,3R,4R,5S,6S)-2-((E)-1'-benzyl-3,3'-dioxo-1',3'-dihydro-3H-[2,2']biindolyliden-1-yl)-4,5-bis-(2,2-dimethyl-propionyloxy)-6-methyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (2R,3R,4R,5S,6S)-2-((E)-1'-benzyl-3,3'-dioxo-1',3'-dihydro-3H-[2,2']biindolyliden-1-yl)-4,5-bis-(2,2-dimethyl-propionyloxy)-6-methyl-tetrahydro-pyran-3-yl ester
• CAS No.: 877458-72-5
• Molecular Formula: C₄₄H₅₀N₂O₉
• Molecular Weight: 750.889

Synonyms:

Chemical Property of 2,2-Dimethyl-propionic acid (2R,3R,4R,5S,6S)-2-((E)-1'-benzyl-3,3'-dioxo-1',3'-dihydro-3H-[2,2']biindolyliden-1-yl)-4,5-bis-(2,2-dimethyl-propionyloxy)-6-methyl-tetrahydro-pyran-3-yl ester

Chemical Property:

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Safty Information:

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MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-propionic acid (2R,3R,4R,5S,6S)-2-((E)-1'-benzyl-3,3'-dioxo-1',3'-dihydro-3H-[2,2']biindolyliden-1-yl)-4,5-bis-(2,2-dimethyl-propionyloxy)-6-methyl-tetrahydro-pyran-3-yl ester

There total 5 articles about 2,2-Dimethyl-propionic acid (2R,3R,4R,5S,6S)-2-((E)-1'-benzyl-3,3'-dioxo-1',3'-dihydro-3H-[2,2']biindolyliden-1-yl)-4,5-bis-(2,2-dimethyl-propionyloxy)-6-methyl-tetrahydro-pyran-3-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:

2,2-Dimethyl-propionic acid (2S,3R,4R,5S,6S)-2-(1-benzyl-3'-oxo-1H,3'H-[2,2']biindolyl-3-yloxy)-4,5-bis-(2,2-dimethyl-propionyloxy)-6-methyl-tetrahydro-pyran-3-yl ester → 2,2-Dimethyl-propionic acid (2R,3R,4R,5S,6S)-2-((E)-1'-benzyl-3,3'-dioxo-1',3'-dihydro-3H-[2,2']biindolyliden-1-yl)-4,5-bis-(2,2-dimethyl-propionyloxy)-6-methyl-tetrahydro-pyran-3-yl ester (877458-72-5)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at -20 - 20 ℃;

DOI:10.1055/s-2005-918489

Reference yield:

benzyl bromide (100-39-0) → 2,2-Dimethyl-propionic acid (2R,3R,4R,5S,6S)-2-((E)-1'-benzyl-3,3'-dioxo-1',3'-dihydro-3H-[2,2']biindolyliden-1-yl)-4,5-bis-(2,2-dimethyl-propionyloxy)-6-methyl-tetrahydro-pyran-3-yl ester (877458-72-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaH / dimethylformamide / 1 h / 20 °C

1.2: 30 percent / dimethylformamide / 1 h / 20 °C

2.1: 4 Angstroem molecular sieves; TMSOTf / CH₂Cl₂ / 1.5 h / -20 °C

3.1: 73 mg / 4 Angstroem molecular sieves; TMSOTf / CH₂Cl₂ / -20 - 20 °C

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium hydride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1055/s-2005-918489

Reference yield:

N-benzylindigo → 2,2-Dimethyl-propionic acid (2R,3R,4R,5S,6S)-2-((E)-1'-benzyl-3,3'-dioxo-1',3'-dihydro-3H-[2,2']biindolyliden-1-yl)-4,5-bis-(2,2-dimethyl-propionyloxy)-6-methyl-tetrahydro-pyran-3-yl ester (877458-72-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 4 Angstroem molecular sieves; TMSOTf / CH₂Cl₂ / 1.5 h / -20 °C

2: 73 mg / 4 Angstroem molecular sieves; TMSOTf / CH₂Cl₂ / -20 - 20 °C

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane;

DOI:10.1055/s-2005-918489

upstream raw materials:

benzyl bromide

1H,1H'-2,2'-Biindolylidene-3,3'-dione

2,3,4-tri-O-pivaloyl-α-L-rhamnopyranosyl trichloroacetimidate

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