Hexanoic acid (R)-11-[bis-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl)-carbamoyl]-1-hexyl-undecyl ester

Base Information

• Chemical Name: Hexanoic acid (R)-11-[bis-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl)-carbamoyl]-1-hexyl-undecyl ester
• CAS No.: 887624-19-3
• Molecular Formula: C₈₀H₁₀₇NO₁₃
• Molecular Weight: 1290.73
• Mol file: 887624-19-3.mol

Synonyms:Hexanoic acid (R)-11-[bis-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl)-carbamoyl]-1-hexyl-undecyl ester

Chemical Property of Hexanoic acid (R)-11-[bis-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl)-carbamoyl]-1-hexyl-undecyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Hexanoic acid (R)-11-[bis-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl)-carbamoyl]-1-hexyl-undecyl ester

There total 8 articles about Hexanoic acid (R)-11-[bis-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl)-carbamoyl]-1-hexyl-undecyl 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: 94.0%

(R)-12-Hydroxy-octadecanoic acid bis-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl)-amide (887624-16-0) + Hexanoyl chloride (142-61-0) → Hexanoic acid (R)-11-[bis-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl)-carbamoyl]-1-hexyl-undecyl ester (887624-19-3)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; for 5.5h;

DOI:10.1021/jo051904b

Reference yield:

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside (53008-65-4,641635-63-4) → Hexanoic acid (R)-11-[bis-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl)-carbamoyl]-1-hexyl-undecyl ester (887624-19-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 78 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

2: Ti(O-iPr)4 / methanol / 3 h / 20 °C

3: 2.34 g / NaBH₃CN / methanol / 48 h / 20 °C

4: 64 percent / N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide / CH₂Cl₂ / 24 h / 20 °C

5: 94 percent / pyridine / CH₂Cl₂ / 5.5 h / 20 °C

With pyridine; titanium(IV) isopropylate; oxalyl dichloride; sodium cyanoborohydride; dimethyl sulfoxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In methanol; dichloromethane;

DOI:10.1021/jo051904b

Reference yield:

bis(methyl 2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranosid-6-yl)amine (887624-14-8) → Hexanoic acid (R)-11-[bis-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl)-carbamoyl]-1-hexyl-undecyl ester (887624-19-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 64 percent / N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide / CH₂Cl₂ / 24 h / 20 °C

2: 94 percent / pyridine / CH₂Cl₂ / 5.5 h / 20 °C

With pyridine; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane;

DOI:10.1021/jo051904b

upstream raw materials:

(R)-12-Hydroxy-octadecanoic acid bis-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl)-amide

Hexanoyl chloride

bis(methyl 2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranosid-6-yl)amine

methyl 6-deoxy-6-amino-2,3,4-tri-O-benzyl-α-D-glucopyranoside