Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-(tert-butyl-diphenyl-silanyloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-(tert-butyl-diphenyl-silanyloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester
• CAS No.: 344403-86-7
• Molecular Formula: C₃₆H₃₉NO₁₀Si
• Molecular Weight: 673.792

Synonyms:

Chemical Property of Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-(tert-butyl-diphenyl-silanyloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-(tert-butyl-diphenyl-silanyloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester

There total 1 articles about Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-(tert-butyl-diphenyl-silanyloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-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:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose (10022-13-6) → Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-(tert-butyl-diphenyl-silanyloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester (344403-86-7)

Guidance literature:

Multi-step reaction with 2 steps

1: NH₂NH₂; AcOH / dimethylformamide

2: imidazole; 4-dimethylaminopyridine / dimethylformamide

With 1H-imidazole; dmap; acetic acid; hydrazine; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(01)00342-2

Reference yield:

Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-(tert-butyl-diphenyl-silanyloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester (344403-86-7) → N-[3-acetylamino-5-(7-acetylamino-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-4-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl]-2-tert-butoxycarbonylamino-succinamic acid

Guidance literature:

Multi-step reaction with 11 steps

1: t-BuOK / methanol; tetrahydrofuran

2: camphorsulfonic acid / acetonitrile

3: NaH / dimethylformamide

4: tetrabutylammonium fluoride; AcOH / tetrahydrofuran

5: dimethylaminosulfur trifluoride / tetrahydrofuran

6: 81 percent / Cp₂HfCl₂; AgClO₄ / CH₂Cl₂

7: ethylenediamine / butan-1-ol

8: methanol

9: H₂ / Pd/C(ethylenediamine poisoned) / CH₂Cl₂; methanol

10: 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide / CH₂Cl₂

11: 84 percent / N-methylaniline / Pd(PPh₃)4 / tetrahydrofuran

With bis(cyclopentadienyl)hafnium dichloride; dimethylaminosulphur trifluoride; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; silver perchlorate; sodium hydride; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; ethylenediamine; N-methylaniline; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; butan-1-ol;

DOI:10.1016/S0040-4039(01)00342-2

Reference yield:

Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-(tert-butyl-diphenyl-silanyloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester (344403-86-7) → N-[(2R,4aR,6S,7R,8R,8aS)-6-((2R,3S,4R,5R,6R)-5-Acetylamino-6-amino-4-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

Guidance literature:

Multi-step reaction with 9 steps

1: t-BuOK / methanol; tetrahydrofuran

2: camphorsulfonic acid / acetonitrile

3: NaH / dimethylformamide

4: tetrabutylammonium fluoride; AcOH / tetrahydrofuran

5: dimethylaminosulfur trifluoride / tetrahydrofuran

6: 81 percent / Cp₂HfCl₂; AgClO₄ / CH₂Cl₂

7: ethylenediamine / butan-1-ol

8: methanol

9: H₂ / Pd/C(ethylenediamine poisoned) / CH₂Cl₂; methanol

With bis(cyclopentadienyl)hafnium dichloride; dimethylaminosulphur trifluoride; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; silver perchlorate; sodium hydride; acetic acid; ethylenediamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; butan-1-ol;

DOI:10.1016/S0040-4039(01)00342-2

upstream raw materials:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose

Downstream raw materials:

2-[(2S,3R,4R,5S,6R)-2-(tert-Butyl-diphenyl-silanyloxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride

3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranose

2-[(2R,4aR,6S,7R,8R,8aS)-6-(tert-Butyl-diphenyl-silanyloxy)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-isoindole-1,3-dione

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