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

Base Information

Chemical Name:5-(methoxycarbonyl)pentyl 2-O-benzoyl-3-O-chloroacetyl-4-O-stearoyl-α-L-rhamnopyranoside
CAS No.:270075-70-2
Molecular Formula:C₄₀H₆₃ClO₁₀
Molecular Weight:739.387
Hs Code.:

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

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

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

There total 10 articles about 5-(methoxycarbonyl)pentyl 2-O-benzoyl-3-O-chloroacetyl-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: 89.0%

: 4547-43-7
methyl 6-hydroxycaproate

: 270075-69-9
2-O-benzoyl-3-O-chloroacetyl-4-O-stearoyl-L-rhamnopyranosyl trichloroacetimidate

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

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 0.166667h;
DOI:10.1016/S0957-4166(99)00553-4

Reference yield:

: 1214-98-8,105026-40-2,127061-11-4,131724-82-8
phenyl 1-thio-α-L-rhamnopyranose

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

Guidance literature:: Multi-step reaction with 9 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

With pyridine; trimethylsilyl trifluoromethanesulfonate; water; mercury(II) trifluoroacetate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; scandium tris(trifluoromethanesulfonate); In methanol; dichloromethane; acetone; 1: Condensation / 2: Esterification / 3: Hydrolysis / 4: Etherification / 5: Hydrolysis / 6: Acylation / 7: Hydrolysis / 8: Addition / 9: Condensation;
DOI:10.1016/S0957-4166(99)00553-4

Reference yield:

: 131087-35-9
phenyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside

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

Guidance literature:: Multi-step reaction with 8 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

With pyridine; trimethylsilyl trifluoromethanesulfonate; water; mercury(II) trifluoroacetate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; scandium tris(trifluoromethanesulfonate); In methanol; dichloromethane; 1: Esterification / 2: Hydrolysis / 3: Etherification / 4: Hydrolysis / 5: Acylation / 6: Hydrolysis / 7: Addition / 8: Condensation;
DOI:10.1016/S0957-4166(99)00553-4