Acetic acid (2R,3S,4R,5S,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[4-(4-trimethylsilanylethynyl-benzoylamino)-butyl]-tetrahydro-pyran-4-yl ester

Base Information

Chemical Name:Acetic acid (2R,3S,4R,5S,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[4-(4-trimethylsilanylethynyl-benzoylamino)-butyl]-tetrahydro-pyran-4-yl ester
CAS No.:289700-07-8
Molecular Formula:C₃₀H₄₁NO₁₀Si
Molecular Weight:603.742
Hs Code.:

Synonyms:Acetic acid (2R,3S,4R,5S,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[4-(4-trimethylsilanylethynyl-benzoylamino)-butyl]-tetrahydro-pyran-4-yl ester

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Chemical Property of Acetic acid (2R,3S,4R,5S,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[4-(4-trimethylsilanylethynyl-benzoylamino)-butyl]-tetrahydro-pyran-4-yl ester

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Technology Process of Acetic acid (2R,3S,4R,5S,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[4-(4-trimethylsilanylethynyl-benzoylamino)-butyl]-tetrahydro-pyran-4-yl ester

There total 5 articles about Acetic acid (2R,3S,4R,5S,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[4-(4-trimethylsilanylethynyl-benzoylamino)-butyl]-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: 75.0%

: 289700-06-7
Acetic acid (2R,3S,4R,5S,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[4-(4-iodo-benzoylamino)-butyl]-tetrahydro-pyran-4-yl ester

: 1066-54-2
trimethylsilylacetylene

: 289700-07-8
Acetic acid (2R,3S,4R,5S,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[4-(4-trimethylsilanylethynyl-benzoylamino)-butyl]-tetrahydro-pyran-4-yl ester

Guidance literature:: With triethylamine; Pf(PPh₃)2Cl₂; In N,N-dimethyl-formamide; at 65 ℃; for 8h;
DOI:10.1055/s-2000-6266

Reference yield:

: 619-58-9
4-iodobenzoic acid

: 289700-07-8
Acetic acid (2R,3S,4R,5S,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[4-(4-trimethylsilanylethynyl-benzoylamino)-butyl]-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 80 percent / HOBt; EDC; DIPEA / dimethylformamide / 12 h / 20 °C

2: 75 percent / Et₃N / Pf(PPh₃)2Cl₂ / dimethylformamide / 8 h / 65 °C

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; Pf(PPh₃)2Cl₂; In N,N-dimethyl-formamide; 1: Acylation / 2: Sonogashira coupling reaction;
DOI:10.1055/s-2000-6266

Reference yield:

: 53263-18-6,82659-53-8,98920-46-8,98920-48-0,98920-49-1,103773-87-1,98920-44-6
allyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside

: 289700-07-8
Acetic acid (2R,3S,4R,5S,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[4-(4-trimethylsilanylethynyl-benzoylamino)-butyl]-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 45 percent / Grubbs' catalyst / CH₂Cl₂ / 12 h / Heating

2: 92 percent / H₂ / 10 percent Pd/C / methanol / 3 h / 20 °C / 760 Torr

3: 80 percent / HOBt; EDC; DIPEA / dimethylformamide / 12 h / 20 °C

4: 75 percent / Et₃N / Pf(PPh₃)2Cl₂ / dimethylformamide / 8 h / 65 °C

With hydrogen; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; Grubbs catalyst first generation; Pf(PPh₃)2Cl₂; In methanol; dichloromethane; N,N-dimethyl-formamide; 1: Cross-metathesis reaction / 2: Catalytic hydrogenation / 3: Acylation / 4: Sonogashira coupling reaction;
DOI:10.1055/s-2000-6266