Benzoic acid (2R,3R,4S,5R,6R)-4-benzyloxy-6-benzyloxymethyl-2-((E)-(2S,3R)-3-benzyloxy-2-octadecanoylamino-octadec-4-enyloxy)-5-(2-chloro-acetoxy)-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,3R,4S,5R,6R)-4-benzyloxy-6-benzyloxymethyl-2-((E)-(2S,3R)-3-benzyloxy-2-octadecanoylamino-octadec-4-enyloxy)-5-(2-chloro-acetoxy)-tetrahydro-pyran-3-yl ester
• CAS No.: 201139-13-1
• Molecular Formula: C₇₂H₁₀₄ClNO₁₀
• Molecular Weight: 1179.07
• Mol file: 201139-13-1.mol

Synonyms:Benzoic acid (2R,3R,4S,5R,6R)-4-benzyloxy-6-benzyloxymethyl-2-((E)-(2S,3R)-3-benzyloxy-2-octadecanoylamino-octadec-4-enyloxy)-5-(2-chloro-acetoxy)-tetrahydro-pyran-3-yl ester

Chemical Property of Benzoic acid (2R,3R,4S,5R,6R)-4-benzyloxy-6-benzyloxymethyl-2-((E)-(2S,3R)-3-benzyloxy-2-octadecanoylamino-octadec-4-enyloxy)-5-(2-chloro-acetoxy)-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2R,3R,4S,5R,6R)-4-benzyloxy-6-benzyloxymethyl-2-((E)-(2S,3R)-3-benzyloxy-2-octadecanoylamino-octadec-4-enyloxy)-5-(2-chloro-acetoxy)-tetrahydro-pyran-3-yl ester

There total 10 articles about Benzoic acid (2R,3R,4S,5R,6R)-4-benzyloxy-6-benzyloxymethyl-2-((E)-(2S,3R)-3-benzyloxy-2-octadecanoylamino-octadec-4-enyloxy)-5-(2-chloro-acetoxy)-tetrahydro-pyran-3-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: 74.0%

Octadecanoic acid ((E)-(1S,2R)-2-benzyloxy-1-hydroxymethyl-heptadec-3-enyl)-amide (201139-02-8) + C33H40ClN2O9P (201139-12-0) → Benzoic acid (2R,3R,4S,5R,6R)-4-benzyloxy-6-benzyloxymethyl-2-((E)-(2S,3R)-3-benzyloxy-2-octadecanoylamino-octadec-4-enyloxy)-5-(2-chloro-acetoxy)-tetrahydro-pyran-3-yl ester (201139-13-1)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1016/S0040-4039(97)10365-3

Reference yield:

Octadecanoic acid ((E)-(1S,2R)-2-benzyloxy-1-hydroxymethyl-heptadec-3-enyl)-amide (201139-02-8) + Benzoic acid (2R,3R,4S,5R,6R)-4-benzyloxy-6-benzyloxymethyl-5-(2-chloro-acetoxy)-2-(diphenoxy-phosphoryloxy)-tetrahydro-pyran-3-yl ester → Benzoic acid (2R,3R,4S,5R,6R)-4-benzyloxy-6-benzyloxymethyl-2-((E)-(2S,3R)-3-benzyloxy-2-octadecanoylamino-octadec-4-enyloxy)-5-(2-chloro-acetoxy)-tetrahydro-pyran-3-yl ester (201139-13-1)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1016/S0040-4039(00)01343-5

Reference yield:

benzoyl chloride (98-88-4) → Benzoic acid (2R,3R,4S,5R,6R)-4-benzyloxy-6-benzyloxymethyl-2-((E)-(2S,3R)-3-benzyloxy-2-octadecanoylamino-octadec-4-enyloxy)-5-(2-chloro-acetoxy)-tetrahydro-pyran-3-yl ester (201139-13-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 97 percent / DMAP, pyridine / CH₂Cl₂ / 2 h

2: 96 percent / NaBH₃CN, satd. HCl, 3A mol. sieves / diethyl ether; tetrahydrofuran / 0.5 h / 0 °C

3: 97 percent / pyridine / CH₂Cl₂ / 2 h / 0 °C

4: 76 percent / PdCl₂, NaOAc / acetic acid; H₂O / 1 h / 80 °C

5: 66 percent / 1.) n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / -10 °C / 1.) -78 deg C, 15 min

6: 74 percent / TMSOTf / CH₂Cl₂ / 1 h / 0 °C

With pyridine; hydrogenchloride; dmap; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; sodium acetate; sodium cyanoborohydride; palladium dichloride; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; water; acetic acid;

DOI:10.1016/S0040-4039(97)10365-3

upstream raw materials:

Octadecanoic acid ((E)-(1S,2R)-2-benzyloxy-1-hydroxymethyl-heptadec-3-enyl)-amide

C₃₃H₄₀ClN₂O₉P

benzoyl chloride

Stearoyl chloride

Downstream raw materials:

Benzoic acid (2R,3R,4S,5R,6R)-4-benzyloxy-6-benzyloxymethyl-2-((E)-(2S,3R)-3-benzyloxy-2-octadecanoylamino-octadec-4-enyloxy)-5-hydroxy-tetrahydro-pyran-3-yl ester