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

Base Information

• Chemical Name: (R)-12-Hydroxy-octadecanoic acid bis-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl)-amide
• CAS No.: 887624-16-0
• Molecular Formula: C₇₄H₉₇NO₁₂
• Molecular Weight: 1192.58
• Mol file: 887624-16-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about (R)-12-Hydroxy-octadecanoic acid bis-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl)-amide 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: 64.0%

bis(methyl 2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranosid-6-yl)amine (887624-14-8) + R-12-hydroxyoctadecanoic acid (106-14-9,18417-00-0,36377-33-0,5762-36-7,78642-86-1,8039-23-4,27924-99-8,860114-96-1) → (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)

Guidance literature:

With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1021/jo051904b

Reference yield:

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside (53008-65-4,641635-63-4) → (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)

Guidance literature:

Multi-step reaction with 4 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

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

DOI:10.1021/jo051904b

Reference yield:

((2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl)-[1-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-meth-(E)-ylidene]-amine → (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)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.34 g / NaBH₃CN / methanol / 48 h / 20 °C

2: 64 percent / N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide / CH₂Cl₂ / 24 h / 20 °C

With sodium cyanoborohydride; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In methanol; dichloromethane;

DOI:10.1021/jo051904b

upstream raw materials:

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

R-12-hydroxyoctadecanoic acid

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

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside

Downstream raw materials:

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