(2S,3S,4S,5R,6S)-3,4,5-Tris-allyloxycarbonyloxy-6-[4-({methyl-[2-(4-nitro-phenoxycarbonyloxy)-ethyl]-carbamoyloxy}-methyl)-phenylcarbamoyloxy]-tetrahydro-pyran-2-carboxylic acid allyl ester

Base Information

• Chemical Name: (2S,3S,4S,5R,6S)-3,4,5-Tris-allyloxycarbonyloxy-6-[4-({methyl-[2-(4-nitro-phenoxycarbonyloxy)-ethyl]-carbamoyloxy}-methyl)-phenylcarbamoyloxy]-tetrahydro-pyran-2-carboxylic acid allyl ester
• CAS No.: 922173-41-9
• Molecular Formula: C₄₀H₄₃N₃O₂₁
• Molecular Weight: 901.789

Synonyms:(2S,3S,4S,5R,6S)-3,4,5-Tris-allyloxycarbonyloxy-6-[4-({methyl-[2-(4-nitro-phenoxycarbonyloxy)-ethyl]-carbamoyloxy}-methyl)-phenylcarbamoyloxy]-tetrahydro-pyran-2-carboxylic acid allyl ester

Chemical Property of (2S,3S,4S,5R,6S)-3,4,5-Tris-allyloxycarbonyloxy-6-[4-({methyl-[2-(4-nitro-phenoxycarbonyloxy)-ethyl]-carbamoyloxy}-methyl)-phenylcarbamoyloxy]-tetrahydro-pyran-2-carboxylic acid allyl ester

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Technology Process of (2S,3S,4S,5R,6S)-3,4,5-Tris-allyloxycarbonyloxy-6-[4-({methyl-[2-(4-nitro-phenoxycarbonyloxy)-ethyl]-carbamoyloxy}-methyl)-phenylcarbamoyloxy]-tetrahydro-pyran-2-carboxylic acid allyl ester

There total 10 articles about (2S,3S,4S,5R,6S)-3,4,5-Tris-allyloxycarbonyloxy-6-[4-({methyl-[2-(4-nitro-phenoxycarbonyloxy)-ethyl]-carbamoyloxy}-methyl)-phenylcarbamoyloxy]-tetrahydro-pyran-2-carboxylic acid allyl 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: 71.0%

(2S,3S,4S,5R,6S)-3,4,5-Tris-allyloxycarbonyloxy-6-(4-{[(2-hydroxy-ethyl)-methyl-carbamoyloxy]-methyl}-phenylcarbamoyloxy)-tetrahydro-pyran-2-carboxylic acid allyl ester (922173-39-5) + 4-Nitrophenyl chloroformate (7693-46-1) → (2S,3S,4S,5R,6S)-3,4,5-Tris-allyloxycarbonyloxy-6-[4-({methyl-[2-(4-nitro-phenoxycarbonyloxy)-ethyl]-carbamoyloxy}-methyl)-phenylcarbamoyloxy]-tetrahydro-pyran-2-carboxylic acid allyl ester (922173-41-9)

Guidance literature:

With pyridine; In dichloromethane; at 0 - 20 ℃; for 26h;

DOI:10.1021/jo0612675

Reference yield:

4-nitrobenzyl chloride (619-73-8) → (2S,3S,4S,5R,6S)-3,4,5-Tris-allyloxycarbonyloxy-6-[4-({methyl-[2-(4-nitro-phenoxycarbonyloxy)-ethyl]-carbamoyloxy}-methyl)-phenylcarbamoyloxy]-tetrahydro-pyran-2-carboxylic acid allyl ester (922173-41-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 98 percent / imidazole / dimethylformamide / 2 h / 20 °C

2: 84 percent / ammonium formate / Pd/C / ethanol / 5 h / 20 °C

3: 86 percent / triethylamine / toluene / 3 h / 70 °C

4: 69 percent / triethylamine / toluene / 1.5 h / 0 °C

5: 81 percent / acetic acid; TBAF / tetrahydrofuran / 20 h / 20 °C

6: 91 percent / pyridine / CH₂Cl₂ / 2 h / 0 °C

7: 79 percent / DMAP / CH₂Cl₂ / 0.75 h / 0 - 20 °C

8: 71 percent / pyridine / CH₂Cl₂ / 26 h / 0 - 20 °C

With pyridine; 1H-imidazole; dmap; tetrabutyl ammonium fluoride; ammonium formate; acetic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo0612675

Reference yield:

tert-butyldimethyl-4-nitrobenzyloxysilane (135605-97-9) → (2S,3S,4S,5R,6S)-3,4,5-Tris-allyloxycarbonyloxy-6-[4-({methyl-[2-(4-nitro-phenoxycarbonyloxy)-ethyl]-carbamoyloxy}-methyl)-phenylcarbamoyloxy]-tetrahydro-pyran-2-carboxylic acid allyl ester (922173-41-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 84 percent / ammonium formate / Pd/C / ethanol / 5 h / 20 °C

2: 86 percent / triethylamine / toluene / 3 h / 70 °C

3: 69 percent / triethylamine / toluene / 1.5 h / 0 °C

4: 81 percent / acetic acid; TBAF / tetrahydrofuran / 20 h / 20 °C

5: 91 percent / pyridine / CH₂Cl₂ / 2 h / 0 °C

6: 79 percent / DMAP / CH₂Cl₂ / 0.75 h / 0 - 20 °C

7: 71 percent / pyridine / CH₂Cl₂ / 26 h / 0 - 20 °C

With pyridine; dmap; tetrabutyl ammonium fluoride; ammonium formate; acetic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; toluene;

DOI:10.1021/jo0612675

upstream raw materials:

(2S,3S,4S,5R,6S)-3,4,5-Tris-allyloxycarbonyloxy-6-(4-{[(2-hydroxy-ethyl)-methyl-carbamoyloxy]-methyl}-phenylcarbamoyloxy)-tetrahydro-pyran-2-carboxylic acid allyl ester

4-Nitrophenyl chloroformate

allyl 1,2,3,4-tetra-O-(allyloxycarbonyl)-D-glucopyranosiduronate

(2S,3S,4S,5R,6S)-3,4,5-Tris-allyloxycarbonyloxy-6-(4-hydroxymethyl-phenylcarbamoyloxy)-tetrahydro-pyran-2-carboxylic acid allyl ester

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