1-(methoxycarbonyl)pentadec-10(S)-yl 2,3-didehydro-4-O-benzyl-α-L-rhamnopyranosyl-(1→4)-2,3-O-isopropylidene-α-L-rhamnopyranoside

Base Information

• Chemical Name: 1-(methoxycarbonyl)pentadec-10(S)-yl 2,3-didehydro-4-O-benzyl-α-L-rhamnopyranosyl-(1→4)-2,3-O-isopropylidene-α-L-rhamnopyranoside
• CAS No.: 1513847-21-6
• Molecular Formula: C₃₉H₆₂O₉
• Molecular Weight: 674.916
• Mol file: 1513847-21-6.mol

Synonyms:1-(methoxycarbonyl)pentadec-10(S)-yl 2,3-didehydro-4-O-benzyl-α-L-rhamnopyranosyl-(1→4)-2,3-O-isopropylidene-α-L-rhamnopyranoside

Chemical Property of 1-(methoxycarbonyl)pentadec-10(S)-yl 2,3-didehydro-4-O-benzyl-α-L-rhamnopyranosyl-(1→4)-2,3-O-isopropylidene-α-L-rhamnopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(methoxycarbonyl)pentadec-10(S)-yl 2,3-didehydro-4-O-benzyl-α-L-rhamnopyranosyl-(1→4)-2,3-O-isopropylidene-α-L-rhamnopyranoside

There total 10 articles about 1-(methoxycarbonyl)pentadec-10(S)-yl 2,3-didehydro-4-O-benzyl-α-L-rhamnopyranosyl-(1→4)-2,3-O-isopropylidene-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: 96.0%

benzyl bromide (100-39-0) + 1-(methoxycarbonyl)pentadec-10(S)-yl α-L-rhamnopyranoside (182818-70-8) → 1-(methoxycarbonyl)pentadec-10(S)-yl 2,3-didehydro-4-O-benzyl-α-L-rhamnopyranosyl-(1→4)-2,3-O-isopropylidene-α-L-rhamnopyranoside (1513847-21-6)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/ol403369h

Reference yield:

Heptadec-7-yn-6-ol → 1-(methoxycarbonyl)pentadec-10(S)-yl 2,3-didehydro-4-O-benzyl-α-L-rhamnopyranosyl-(1→4)-2,3-O-isopropylidene-α-L-rhamnopyranoside (1513847-21-6)

Guidance literature:

Multi-step reaction with 8 steps

1: potassium hydride; Trimethylenediamine / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

2: 1,8-diazabicyclo[5.4.0]undec-7-ene; dmap / acetonitrile / 2 h / 0 - 20 °C / Inert atmosphere

3: potassium permanganate; acetic acid; cetyltrimethylammonim bromide / benzene; water / 24 h / 0 °C

4: potassium permanganate; acetic acid; cetyltrimethylammonim bromide / benzene; water / 24 h / 0 °C

5: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; triphenylphosphine / dichloromethane / 0 °C / Inert atmosphere

6: CeCl₃*CH₄O; sodium tetrahydroborate / dichloromethane / 2 h / -78 °C / Inert atmosphere

7: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; tert-butyl alcohol; acetone / 0 - 20 °C

8: sodium hydride / N,N-dimethyl-formamide / 2 h / 0 - 20 °C / Inert atmosphere

With dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium tetrahydroborate; potassium permanganate; osmium(VIII) oxide; CeCl₃*CH₄O; cetyltrimethylammonim bromide; potassium hydride; sodium hydride; acetic acid; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; Trimethylenediamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol; benzene; 6: |Luche Cerium Reduction / 7: |Upjohn Dihydroxylation;

DOI:10.1021/ol403369h

Reference yield:

1-undecyne (2243-98-3) → 1-(methoxycarbonyl)pentadec-10(S)-yl 2,3-didehydro-4-O-benzyl-α-L-rhamnopyranosyl-(1→4)-2,3-O-isopropylidene-α-L-rhamnopyranoside (1513847-21-6)

Guidance literature:

Multi-step reaction with 9 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

1.2: 5 h / -78 - 20 °C / Inert atmosphere

2.1: potassium hydride; Trimethylenediamine / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; dmap / acetonitrile / 2 h / 0 - 20 °C / Inert atmosphere

4.1: potassium permanganate; acetic acid; cetyltrimethylammonim bromide / benzene; water / 24 h / 0 °C

5.1: potassium permanganate; acetic acid; cetyltrimethylammonim bromide / benzene; water / 24 h / 0 °C

6.1: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; triphenylphosphine / dichloromethane / 0 °C / Inert atmosphere

7.1: CeCl₃*CH₄O; sodium tetrahydroborate / dichloromethane / 2 h / -78 °C / Inert atmosphere

8.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; tert-butyl alcohol; acetone / 0 - 20 °C

9.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 0 - 20 °C / Inert atmosphere

With dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium tetrahydroborate; potassium permanganate; osmium(VIII) oxide; n-butyllithium; CeCl₃*CH₄O; cetyltrimethylammonim bromide; potassium hydride; sodium hydride; acetic acid; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; Trimethylenediamine; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol; benzene; 7.1: |Luche Cerium Reduction / 8.1: |Upjohn Dihydroxylation;

DOI:10.1021/ol403369h

upstream raw materials:

benzyl bromide

1-(methoxycarbonyl)pentadec-10(S)-yl α-L-rhamnopyranoside

(12S)-12-hydroxy-1-heptadecyne

1-undecyne

Downstream raw materials:

1-(methoxycarbonyl)pentadec-10(S)-yl 4-O-benzyl-α-L-rhamnopyranosyl-(1→4)-2,3-O-isopropylidene-α-L-rhamnopyranoside

1-(hydroxycarbonyl)pentadec-10(S)-yl 4-O-benzyl-α-L-rhamnopyranosyl-(1→4)-2,3-O-isopropylidene-α-L-rhamnopyranoside

C₃₈H₆₀O₁₀

merremoside d