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

Base Information

Chemical Name:3'-(benzyloxy)-6'-<<β-(trimethylsilyl)ethoxy>carbonyl>-5'-(1-heptyn-1-yl)phenyl 2,3-di-O-benzyl-5,6-cyclopentylidene-D-galactofuranoside
CAS No.:137571-82-5
Molecular Formula:C₅₁H₆₂O₉Si
Molecular Weight:847.133
Hs Code.:

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

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

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

There total 16 articles about 3'-(benzyloxy)-6'-<<β-(trimethylsilyl)ethoxy>carbonyl>-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: 90.0%

: 100-39-0
benzyl bromide

: 137571-81-4
3'-(benzyloxy)-6'-<<β-(trimethylsilyl)ethoxy>carbonyl>-5'-(1-heptyn-1-yl)phenyl 3-O-benzyl-5,6-cyclopentylidene-D-galactofuranoside

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

Guidance literature:: With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; for 6h; Ambient temperature;
DOI:10.1021/ja00028a035

Reference yield:

: 628-71-7
1-Heptyne

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

Guidance literature:: Multi-step reaction with 5 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

With dmap; potassium hydroxide; bis(triphenylphosphine)palladium(II)-chloride; 18-crown-6 ether; 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:

: 2916-68-9
2-(Trimethylsilyl)ethanol

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

Guidance literature:: Multi-step reaction with 3 steps

1: 254 mg / 4-DMAP, EDCI / CH₂Cl₂ / 5 h / Ambient temperature

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

3: 90 percent / NaH, tetrabutylammonium iodide / tetrahydrofuran / 6 h / Ambient temperature

With dmap; 18-crown-6 ether; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane; acetone;
DOI:10.1021/ja00028a035