3'-(benzyloxy)-6'-carboxy-5'-(1-heptyn-1-yl)phenyl 2,3-di-O-benzyl-5,6-cyclopentylidene-D-galactofuranoside

Base Information

• Chemical Name: 3'-(benzyloxy)-6'-carboxy-5'-(1-heptyn-1-yl)phenyl 2,3-di-O-benzyl-5,6-cyclopentylidene-D-galactofuranoside
• CAS No.: 137571-83-6
• Molecular Formula: C₄₆H₅₀O₉
• Molecular Weight: 746.898

Synonyms:3'-(benzyloxy)-6'-carboxy-5'-(1-heptyn-1-yl)phenyl 2,3-di-O-benzyl-5,6-cyclopentylidene-D-galactofuranoside

Chemical Property of 3'-(benzyloxy)-6'-carboxy-5'-(1-heptyn-1-yl)phenyl 2,3-di-O-benzyl-5,6-cyclopentylidene-D-galactofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3'-(benzyloxy)-6'-carboxy-5'-(1-heptyn-1-yl)phenyl 2,3-di-O-benzyl-5,6-cyclopentylidene-D-galactofuranoside

There total 16 articles about 3'-(benzyloxy)-6'-carboxy-5'-(1-heptyn-1-yl)phenyl 2,3-di-O-benzyl-5,6-cyclopentylidene-D-galactofuranoside 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%

3'-(benzyloxy)-6'-<<β-(trimethylsilyl)ethoxy>carbonyl>-5'-(1-heptyn-1-yl)phenyl 2,3-di-O-benzyl-5,6-cyclopentylidene-D-galactofuranoside (137571-82-5) → 3'-(benzyloxy)-6'-carboxy-5'-(1-heptyn-1-yl)phenyl 2,3-di-O-benzyl-5,6-cyclopentylidene-D-galactofuranoside (137571-83-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 4h; Ambient temperature;

DOI:10.1021/ja00028a035

Reference yield:

1-Heptyne (628-71-7) → 3'-(benzyloxy)-6'-carboxy-5'-(1-heptyn-1-yl)phenyl 2,3-di-O-benzyl-5,6-cyclopentylidene-D-galactofuranoside (137571-83-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 87 percent / bis(triphenylphosphine)palladium(II) chloride, Et₃N / dimethylformamide / 12 h / 90 °C

2: 48percent aq. KOH / dimethylsulfoxide / 0.5 h / 60 °C

3: 254 mg / 4-DMAP, EDCI / CH₂Cl₂ / 5 h / Ambient temperature

4: K₂CO₃, 18-crown-6 / acetone / 8 h / Heating

5: 90 percent / NaH, tetrabutylammonium iodide / tetrahydrofuran / 6 h / Ambient temperature

6: 96 percent / TBAF / tetrahydrofuran / 4 h / Ambient temperature

With dmap; potassium hydroxide; bis(triphenylphosphine)palladium(II)-chloride; 18-crown-6 ether; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone;

DOI:10.1021/ja00028a035

Reference yield:

acide 2,4,6-trihydroxybenzoique (83-30-7) → 3'-(benzyloxy)-6'-carboxy-5'-(1-heptyn-1-yl)phenyl 2,3-di-O-benzyl-5,6-cyclopentylidene-D-galactofuranoside (137571-83-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 34 percent / trifluoroacetic anhydride / trifluoroacetic acid / 24 h / Ambient temperature

2: 92 percent / triphenylphosphine, DIAD / tetrahydrofuran / 2 h / 0 - 20 °C

3: 85 percent / pyridine / 12 h / 0 °C

4: 87 percent / bis(triphenylphosphine)palladium(II) chloride, Et₃N / dimethylformamide / 12 h / 90 °C

5: 48percent aq. KOH / dimethylsulfoxide / 0.5 h / 60 °C

6: 254 mg / 4-DMAP, EDCI / CH₂Cl₂ / 5 h / Ambient temperature

7: K₂CO₃, 18-crown-6 / acetone / 8 h / Heating

8: 90 percent / NaH, tetrabutylammonium iodide / tetrahydrofuran / 6 h / Ambient temperature

9: 96 percent / TBAF / tetrahydrofuran / 4 h / Ambient temperature

With pyridine; dmap; potassium hydroxide; bis(triphenylphosphine)palladium(II)-chloride; 18-crown-6 ether; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; trifluoroacetic acid;

DOI:10.1021/ja00028a035

upstream raw materials:

3'-(benzyloxy)-6'-<<β-(trimethylsilyl)ethoxy>carbonyl>-5'-(1-heptyn-1-yl)phenyl 2,3-di-O-benzyl-5,6-cyclopentylidene-D-galactofuranoside

1-Heptyne

acide 2,4,6-trihydroxybenzoique

benzyl bromide

Downstream raw materials:

KS-502

3'-(benzyloxy)-6'-<<5''-(1-heptyl)-3''-hydroxyphenoxy>carbonyl>-5'-(1-heptyn-1-yl)phenyl 2,3-di-O-benzyl-D-galactofuranoside

3'-(benzyloxy)-6'-<<4''-<(benzyloxy)carbonyl>-5''-(1-heptyl)-3''-hydroxyphenoxy>carbonyl>-5'-(1-heptyn-1-yl)phenyl 2,3-di-O-benzyl-D-galactofuranoside

KS-501

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