5-(methoxycarbonyl)pentyl 2-O-benzoyl-4-O-stearoyl-α-L-rhamnopyranoside

Base Information

• Chemical Name: 5-(methoxycarbonyl)pentyl 2-O-benzoyl-4-O-stearoyl-α-L-rhamnopyranoside
• CAS No.: 270075-71-3
• Molecular Formula: C₃₈H₆₂O₉
• Molecular Weight: 662.905
• Mol file: 270075-71-3.mol

Synonyms:5-(methoxycarbonyl)pentyl 2-O-benzoyl-4-O-stearoyl-α-L-rhamnopyranoside

Chemical Property of 5-(methoxycarbonyl)pentyl 2-O-benzoyl-4-O-stearoyl-α-L-rhamnopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-(methoxycarbonyl)pentyl 2-O-benzoyl-4-O-stearoyl-α-L-rhamnopyranoside

There total 11 articles about 5-(methoxycarbonyl)pentyl 2-O-benzoyl-4-O-stearoyl-α-L-rhamnopyranoside 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: 86.0%

5-(methoxycarbonyl)pentyl 2-O-benzoyl-3-O-chloroacetyl-4-O-stearoyl-α-L-rhamnopyranoside (270075-70-2) → 5-(methoxycarbonyl)pentyl 2-O-benzoyl-4-O-stearoyl-α-L-rhamnopyranoside (270075-71-3)

Guidance literature:

With pyridine; thiourea; In N,N-dimethyl-formamide; at 23 ℃; for 3h;

DOI:10.1016/S0957-4166(99)00553-4

Reference yield:

phenyl 1-thio-α-L-rhamnopyranose (1214-98-8,105026-40-2,127061-11-4,131724-82-8) → 5-(methoxycarbonyl)pentyl 2-O-benzoyl-4-O-stearoyl-α-L-rhamnopyranoside (270075-71-3)

Guidance literature:

Multi-step reaction with 10 steps

1: 96 percent / scandium trifluoromethanesulfonate / acetone / 2 h / 23 °C

2: pyridine / CH₂Cl₂ / 0.25 h / 0 °C

3: aq. AcOH / 2 h / 50 °C

4: scandium trifluoromethanesulfonate / CH₂Cl₂ / 1 h / 23 °C

5: 90 percent aq. acetic acid / methanol / 8 h / 23 °C

6: 94 percent / C₅H₅N / CH₂Cl₂ / 1 h / 0 °C

7: 76 percent / H₂O; Hg(OCOCF₃)2 / CH₂Cl₂ / 3 h / 23 °C

8: 76 percent / DBU / CH₂Cl₂ / -10 - 20 °C

9: 89 percent / TMSOTf / CH₂Cl₂ / 0.17 h / 0 °C

10: 86 percent / thiourea; C₅H₅N / dimethylformamide / 3 h / 23 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; water; mercury(II) trifluoroacetate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; thiourea; scandium tris(trifluoromethanesulfonate); In methanol; dichloromethane; N,N-dimethyl-formamide; acetone; 1: Condensation / 2: Esterification / 3: Hydrolysis / 4: Etherification / 5: Hydrolysis / 6: Acylation / 7: Hydrolysis / 8: Addition / 9: Condensation / 10: Deacetylation;

DOI:10.1016/S0957-4166(99)00553-4

Reference yield:

phenyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside (131087-35-9) → 5-(methoxycarbonyl)pentyl 2-O-benzoyl-4-O-stearoyl-α-L-rhamnopyranoside (270075-71-3)

Guidance literature:

Multi-step reaction with 9 steps

1: pyridine / CH₂Cl₂ / 0.25 h / 0 °C

2: aq. AcOH / 2 h / 50 °C

3: scandium trifluoromethanesulfonate / CH₂Cl₂ / 1 h / 23 °C

4: 90 percent aq. acetic acid / methanol / 8 h / 23 °C

5: 94 percent / C₅H₅N / CH₂Cl₂ / 1 h / 0 °C

6: 76 percent / H₂O; Hg(OCOCF₃)2 / CH₂Cl₂ / 3 h / 23 °C

7: 76 percent / DBU / CH₂Cl₂ / -10 - 20 °C

8: 89 percent / TMSOTf / CH₂Cl₂ / 0.17 h / 0 °C

9: 86 percent / thiourea; C₅H₅N / dimethylformamide / 3 h / 23 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; water; mercury(II) trifluoroacetate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; thiourea; scandium tris(trifluoromethanesulfonate); In methanol; dichloromethane; N,N-dimethyl-formamide; 1: Esterification / 2: Hydrolysis / 3: Etherification / 4: Hydrolysis / 5: Acylation / 6: Hydrolysis / 7: Addition / 8: Condensation / 9: Deacetylation;

DOI:10.1016/S0957-4166(99)00553-4

upstream raw materials:

5-(methoxycarbonyl)pentyl 2-O-benzoyl-3-O-chloroacetyl-4-O-stearoyl-α-L-rhamnopyranoside

phenyl 1-thio-α-L-rhamnopyranose

phenyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside

orthobenzoic acid trimethyl ester

Downstream raw materials:

5-(methoxycarbonyl)pentyl (4,6-di-O-acetyl-2-azido-3-O-chloroacetyl-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-stearoyl-α-L-rhamnopyranoside

5-(methoxycarbonyl)pentyl 2-azido-3-O-chloroacetyl-2-deoxy-4,6-O-diphenylmethylidene-α-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-stearoyl-α-L-rhamnopyranoside

5-(methoxycarbonyl)pentyl (4,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-stearoyl-α-L-rhamnopyranoside