Octadecanoic acid (2R,3S,4R,5R,6S)-5-acetylamino-6-benzyloxy-4-{[(S)-1-((R)-3-benzyloxycarbonyl-1-carbamoyl-propylcarbamoyl)-propylcarbamoyl]-methoxy}-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: Octadecanoic acid (2R,3S,4R,5R,6S)-5-acetylamino-6-benzyloxy-4-{[(S)-1-((R)-3-benzyloxycarbonyl-1-carbamoyl-propylcarbamoyl)-propylcarbamoyl]-methoxy}-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 210631-20-2
• Molecular Formula: C₅₁H₇₈N₄O₁₂
• Molecular Weight: 939.2

Synonyms:

Chemical Property of Octadecanoic acid (2R,3S,4R,5R,6S)-5-acetylamino-6-benzyloxy-4-{[(S)-1-((R)-3-benzyloxycarbonyl-1-carbamoyl-propylcarbamoyl)-propylcarbamoyl]-methoxy}-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Octadecanoic acid (2R,3S,4R,5R,6S)-5-acetylamino-6-benzyloxy-4-{[(S)-1-((R)-3-benzyloxycarbonyl-1-carbamoyl-propylcarbamoyl)-propylcarbamoyl]-methoxy}-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester

There total 4 articles about Octadecanoic acid (2R,3S,4R,5R,6S)-5-acetylamino-6-benzyloxy-4-{[(S)-1-((R)-3-benzyloxycarbonyl-1-carbamoyl-propylcarbamoyl)-propylcarbamoyl]-methoxy}-3-hydroxy-tetrahydro-pyran-2-ylmethyl 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: 48.0%

stearic acid (57-11-4) + (R)-4-{(S)-2-[2-((2S,3R,4R,5S,6R)-3-Acetylamino-2-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy)-acetylamino]-butyrylamino}-4-carbamoyl-butyric acid benzyl ester (210631-19-9) → Octadecanoic acid (2R,3S,4R,5R,6S)-5-acetylamino-6-benzyloxy-4-{[(S)-1-((R)-3-benzyloxycarbonyl-1-carbamoyl-propylcarbamoyl)-propylcarbamoyl]-methoxy}-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester (210631-20-2)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; for 20h; Ambient temperature;

DOI:10.1135/cccc19980590

Reference yield:

benzyl-2-acetamino-2-deoxy-4,6-O-isopropylidene-3-O-methoxycarbonylmethyl-α-D-glucopyranoside (127528-38-5) → Octadecanoic acid (2R,3S,4R,5R,6S)-5-acetylamino-6-benzyloxy-4-{[(S)-1-((R)-3-benzyloxycarbonyl-1-carbamoyl-propylcarbamoyl)-propylcarbamoyl]-methoxy}-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester (210631-20-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 99 percent / NaOH, H₂O / methanol / 4 h

2: 66 percent / 1-hydroxybenzotriazole monohydrate, N,N'-dicyclohexylcarbodiimide, i-Pr₂NEt / CH₂Cl₂; dimethylformamide / 1.) 0 deg C, 1 h, 2.) 0 deg C, 1 h; r.t., overnight

3: 71 percent / AcOH, H₂O / 2 h / 60 °C

4: 48 percent / N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride, DMAP / dimethylformamide / 20 h / Ambient temperature

With dmap; sodium hydroxide; water; acetic acid; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1135/cccc19980590

Reference yield:

2-(((4aR,6S,7R,8R,8aS)-7-acetamido-6-(benzyloxy)-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-8-yl)oxy)acetic acid (78604-09-8) → Octadecanoic acid (2R,3S,4R,5R,6S)-5-acetylamino-6-benzyloxy-4-{[(S)-1-((R)-3-benzyloxycarbonyl-1-carbamoyl-propylcarbamoyl)-propylcarbamoyl]-methoxy}-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester (210631-20-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 66 percent / 1-hydroxybenzotriazole monohydrate, N,N'-dicyclohexylcarbodiimide, i-Pr₂NEt / CH₂Cl₂; dimethylformamide / 1.) 0 deg C, 1 h, 2.) 0 deg C, 1 h; r.t., overnight

2: 71 percent / AcOH, H₂O / 2 h / 60 °C

3: 48 percent / N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride, DMAP / dimethylformamide / 20 h / Ambient temperature

With dmap; water; acetic acid; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1135/cccc19980590

upstream raw materials:

stearic acid

(R)-4-{(S)-2-[2-((2S,3R,4R,5S,6R)-3-Acetylamino-2-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy)-acetylamino]-butyrylamino}-4-carbamoyl-butyric acid benzyl ester

benzyl-2-acetamino-2-deoxy-4,6-O-isopropylidene-3-O-methoxycarbonylmethyl-α-D-glucopyranoside

2-(((4aR,6S,7R,8R,8aS)-7-acetamido-6-(benzyloxy)-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-8-yl)oxy)acetic acid

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