(6RS,13R)-6-acetoxy-13-benzyloxy-1-tetrahydropyranyloxytetradec-4-yne

Base Information

• Chemical Name: (6RS,13R)-6-acetoxy-13-benzyloxy-1-tetrahydropyranyloxytetradec-4-yne
• CAS No.: 202405-22-9
• Molecular Formula: C₂₈H₄₂O₅
• Molecular Weight: 458.638
• Mol file: 202405-22-9.mol

Synonyms:(6RS,13R)-6-acetoxy-13-benzyloxy-1-tetrahydropyranyloxytetradec-4-yne

Chemical Property of (6RS,13R)-6-acetoxy-13-benzyloxy-1-tetrahydropyranyloxytetradec-4-yne

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6RS,13R)-6-acetoxy-13-benzyloxy-1-tetrahydropyranyloxytetradec-4-yne

There total 11 articles about (6RS,13R)-6-acetoxy-13-benzyloxy-1-tetrahydropyranyloxytetradec-4-yne 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%

acetic anhydride (108-24-7) + (6RS,13R)-6-hydroxy-13-benzyloxy-1-tetrahydropyranyloxytetradec-4-yne (202405-21-8) → (6RS,13R)-6-acetoxy-13-benzyloxy-1-tetrahydropyranyloxytetradec-4-yne (202405-22-9)

Guidance literature:

With pyridine; for 14h;

Reference yield:

1,8-Octanediol (629-41-4) → (6RS,13R)-6-acetoxy-13-benzyloxy-1-tetrahydropyranyloxytetradec-4-yne (202405-22-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 48 percent / Et₃N, DMAP / CH₂Cl₂ / 6 h

2: 84 percent / PCC, NaOAc / CH₂Cl₂ / 3 h

3: 89 percent / diethyl ether / 3 h / 0 °C

4: porcine pancreatic lipase / diisopropyl ether / 18 h

5: 97 percent / 2N alcoholic KOH / 12 h / Ambient temperature

6: 1.) NaH / 1.) THF, 60 deg C, 1 h, 2.) THF, RT, overnight

7: 88 percent / Bu₄NF / tetrahydrofuran / -78 °C

8: 84 percent / PCC, NaOAc / CH₂Cl₂ / 3 h

9: 1.) n-BuLi / 1.) THF, hexane, -25 deg C, 1 h, 2.) THF, hexane, a) -30 deg C, 4 h, b) RT, 12 h

10: 96 percent / pyridine / 14 h

With pyridine; dmap; potassium hydroxide; n-butyllithium; porcine pancreatic lipase; tetrabutyl ammonium fluoride; sodium acetate; sodium hydride; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; dichloromethane; di-isopropyl ether;

Reference yield:

8-(tert-butyl)dimethylsilyloxyoctanal (128622-13-9) → (6RS,13R)-6-acetoxy-13-benzyloxy-1-tetrahydropyranyloxytetradec-4-yne (202405-22-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 89 percent / diethyl ether / 3 h / 0 °C

2: porcine pancreatic lipase / diisopropyl ether / 18 h

3: 97 percent / 2N alcoholic KOH / 12 h / Ambient temperature

4: 1.) NaH / 1.) THF, 60 deg C, 1 h, 2.) THF, RT, overnight

5: 88 percent / Bu₄NF / tetrahydrofuran / -78 °C

6: 84 percent / PCC, NaOAc / CH₂Cl₂ / 3 h

7: 1.) n-BuLi / 1.) THF, hexane, -25 deg C, 1 h, 2.) THF, hexane, a) -30 deg C, 4 h, b) RT, 12 h

8: 96 percent / pyridine / 14 h

With pyridine; potassium hydroxide; n-butyllithium; porcine pancreatic lipase; tetrabutyl ammonium fluoride; sodium acetate; sodium hydride; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; dichloromethane; di-isopropyl ether;

upstream raw materials:

acetic anhydride

(6RS,13R)-6-hydroxy-13-benzyloxy-1-tetrahydropyranyloxytetradec-4-yne

1,8-Octanediol

8-(tert-butyl)dimethylsilyloxyoctanal

Downstream raw materials:

(E)-(R)-8-Acetoxy-15-benzyloxy-hexadec-2-en-6-ynoic acid ethyl ester

(6RS,13R)-6-acetoxy-13-benzyloxytetradec-4-ynal

(6RS,13R)-6-acetoxy-13-benzyloxytetradec-4-yn-1-ol