Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((Z)-8-benzyloxy-1-vinyl-deca-4,9-dienyloxy)-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((Z)-8-benzyloxy-1-vinyl-deca-4,9-dienyloxy)-tetrahydro-pyran-3-yl ester
• CAS No.: 801237-26-3
• Molecular Formula: C₄₈H₅₆O₈
• Molecular Weight: 760.968
• Mol file: 801237-26-3.mol

Synonyms:Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((Z)-8-benzyloxy-1-vinyl-deca-4,9-dienyloxy)-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((Z)-8-benzyloxy-1-vinyl-deca-4,9-dienyloxy)-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((Z)-8-benzyloxy-1-vinyl-deca-4,9-dienyloxy)-tetrahydro-pyran-3-yl ester

There total 7 articles about Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((Z)-8-benzyloxy-1-vinyl-deca-4,9-dienyloxy)-tetrahydro-pyran-3-yl ester 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: 70.0%

2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl trichloroacetimidate (108869-64-3,130177-78-5,129163-12-8) + (Z)-10-Benzyloxy-dodeca-1,6,11-trien-3-ol → Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((Z)-8-benzyloxy-1-vinyl-deca-4,9-dienyloxy)-tetrahydro-pyran-3-yl ester (801237-26-3)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -20 ℃;

DOI:10.1055/s-2004-831301

Reference yield:

1,5-cis,cis-cyclooctadiene (1552-12-1,111-78-4) → Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((Z)-8-benzyloxy-1-vinyl-deca-4,9-dienyloxy)-tetrahydro-pyran-3-yl ester (801237-26-3)

Guidance literature:

Multi-step reaction with 7 steps

1: m-CPBA / CH₂Cl₂ / 0 - 20 °C

2: aq. H₅IO₆ / dioxane / 1 h / 0 - 20 °C

3: 16.0 g / diethyl ether; tetrahydrofuran / 1 h / 0 - 20 °C

4: 64 percent / pyridine

5: NaH; tetra-n-butylammonium triflate / dimethylformamide

6: TFA; triethylsilane / CH₂Cl₂

7: 70 percent / trimethylsilyl triflate / CH₂Cl₂ / -20 °C

With pyridine; triethylsilane; trimethylsilyl trifluoromethanesulfonate; sodium hydride; tetrabutylammonium trifluoromethylsulfonate; periodic acid; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 3: Grignard reaction;

DOI:10.1055/s-2004-831301

Reference yield:

(Z)-9-oxabicyclo[6.1.0]non-4-ene (19740-90-0,57378-34-4,65207-47-8,73176-71-3,73176-86-0,117468-08-3,637-90-1) → Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((Z)-8-benzyloxy-1-vinyl-deca-4,9-dienyloxy)-tetrahydro-pyran-3-yl ester (801237-26-3)

Guidance literature:

Multi-step reaction with 6 steps

1: aq. H₅IO₆ / dioxane / 1 h / 0 - 20 °C

2: 16.0 g / diethyl ether; tetrahydrofuran / 1 h / 0 - 20 °C

3: 64 percent / pyridine

4: NaH; tetra-n-butylammonium triflate / dimethylformamide

5: TFA; triethylsilane / CH₂Cl₂

6: 70 percent / trimethylsilyl triflate / CH₂Cl₂ / -20 °C

With pyridine; triethylsilane; trimethylsilyl trifluoromethanesulfonate; sodium hydride; tetrabutylammonium trifluoromethylsulfonate; periodic acid; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 2: Grignard reaction;

DOI:10.1055/s-2004-831301

upstream raw materials:

2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl trichloroacetimidate

1,5-cis,cis-cyclooctadiene

(Z)-9-oxabicyclo[6.1.0]non-4-ene

(Z)-oct-4-enedial

Downstream raw materials:

cyclopent-1-enyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside

[(cyclopent-2-en-1-yloxy)methyl]benzene

Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(cyclopent-2-enyloxy)-tetrahydro-pyran-3-yl ester