Acetic acid (Z)-(S)-1-[(2R,7R)-7-((S)-1-benzyloxy-propyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-5-(tetrahydro-pyran-2-yloxy)-pent-3-enyl ester

Base Information

• Chemical Name: Acetic acid (Z)-(S)-1-[(2R,7R)-7-((S)-1-benzyloxy-propyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-5-(tetrahydro-pyran-2-yloxy)-pent-3-enyl ester
• CAS No.: 333788-87-7
• Molecular Formula: C₂₈H₄₀O₆
• Molecular Weight: 472.622
• Mol file: 333788-87-7.mol

Synonyms:Acetic acid (Z)-(S)-1-[(2R,7R)-7-((S)-1-benzyloxy-propyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-5-(tetrahydro-pyran-2-yloxy)-pent-3-enyl ester

Chemical Property of Acetic acid (Z)-(S)-1-[(2R,7R)-7-((S)-1-benzyloxy-propyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-5-(tetrahydro-pyran-2-yloxy)-pent-3-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (Z)-(S)-1-[(2R,7R)-7-((S)-1-benzyloxy-propyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-5-(tetrahydro-pyran-2-yloxy)-pent-3-enyl ester

There total 22 articles about Acetic acid (Z)-(S)-1-[(2R,7R)-7-((S)-1-benzyloxy-propyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-5-(tetrahydro-pyran-2-yloxy)-pent-3-enyl 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: 97.0%

acetic anhydride (108-24-7) + (Z)-(S)-1-[(2R,7R)-7-((S)-1-Benzyloxy-propyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-5-(tetrahydro-pyran-2-yloxy)-pent-3-en-1-ol (333788-86-6) → Acetic acid (Z)-(S)-1-[(2R,7R)-7-((S)-1-benzyloxy-propyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-5-(tetrahydro-pyran-2-yloxy)-pent-3-enyl ester (333788-87-7)

Guidance literature:

With dmap; TEA; In dichloromethane;

DOI:10.1016/S0040-4039(00)02281-4

Reference yield:

2-O-benzyl-3,4-O-isopropylidene-L-threitol (84379-53-3) → Acetic acid (Z)-(S)-1-[(2R,7R)-7-((S)-1-benzyloxy-propyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-5-(tetrahydro-pyran-2-yloxy)-pent-3-enyl ester (333788-87-7)

Guidance literature:

Multi-step reaction with 19 steps

1: 100 percent / TEA; DMAP / CH₂Cl₂

2: 93 percent / diethyl ether / -65 - 0 °C

3: 97 percent / PPTS / ethanol / 80 °C

4: 100 percent / TEA; DMAP / CH₂Cl₂ / 60 °C

5: 98 percent / TEA; DMAP / CH₂Cl₂

6: 96 percent / TBAF / tetrahydrofuran

7: 93 percent / EDA / dimethylsulfoxide / 0 °C

8: 98 percent / AgNO₃; pyridine / acetonitrile

9: 78 percent / n-BuLi; BF₃*OEt₂ / tetrahydrofuran / -78 °C

10: 99 percent / H₂; quinoline / Lindlar cat. / methanol

11: 98 percent / TEA; DMAP / CH₂Cl₂

12: 91 percent / TBAF / tetrahydrofuran / 50 °C

13: 75 percent / (Bu₃Sn)2O; Zn(OTf)2O / toluene / Heating

14: 100 percent / TEA; DMAP / CH₂Cl₂

15: 93 percent / PhSH; ZnCl₂ / CH₂Cl₂ / 0 °C

16: 98 percent / K₂CO₃ / methanol; CH₂Cl₂

17: 99 percent / n-BuLi; BF₃*OEt₂ / -78 °C

18: 100 percent / H₂; quinoline / Lindlar catalyst / ethyl acetate

19: 97 percent / TEA; DMAP / CH₂Cl₂

With pyridine; quinoline; diazoacetic acid ethyl ester; dmap; n-butyllithium; TEA; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; zinc trifluoromethanesulfonate; potassium carbonate; silver nitrate; thiophenol; bis(tri-n-butyltin)oxide; zinc(II) chloride; Lindlar's catalyst; Lindlar catalyst; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; toluene; acetonitrile; 9: Yamaguchi coupling reaction;

DOI:10.1016/S0040-4039(00)02281-4

Reference yield:

(S)-2-(benzyloxy)-2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl 4-methylbenzenesulfonate (131446-96-3) → Acetic acid (Z)-(S)-1-[(2R,7R)-7-((S)-1-benzyloxy-propyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-5-(tetrahydro-pyran-2-yloxy)-pent-3-enyl ester (333788-87-7)

Guidance literature:

Multi-step reaction with 18 steps

1: 93 percent / diethyl ether / -65 - 0 °C

2: 97 percent / PPTS / ethanol / 80 °C

3: 100 percent / TEA; DMAP / CH₂Cl₂ / 60 °C

4: 98 percent / TEA; DMAP / CH₂Cl₂

5: 96 percent / TBAF / tetrahydrofuran

6: 93 percent / EDA / dimethylsulfoxide / 0 °C

7: 98 percent / AgNO₃; pyridine / acetonitrile

8: 78 percent / n-BuLi; BF₃*OEt₂ / tetrahydrofuran / -78 °C

9: 99 percent / H₂; quinoline / Lindlar cat. / methanol

10: 98 percent / TEA; DMAP / CH₂Cl₂

11: 91 percent / TBAF / tetrahydrofuran / 50 °C

12: 75 percent / (Bu₃Sn)2O; Zn(OTf)2O / toluene / Heating

13: 100 percent / TEA; DMAP / CH₂Cl₂

14: 93 percent / PhSH; ZnCl₂ / CH₂Cl₂ / 0 °C

15: 98 percent / K₂CO₃ / methanol; CH₂Cl₂

16: 99 percent / n-BuLi; BF₃*OEt₂ / -78 °C

17: 100 percent / H₂; quinoline / Lindlar catalyst / ethyl acetate

18: 97 percent / TEA; DMAP / CH₂Cl₂

With pyridine; quinoline; diazoacetic acid ethyl ester; dmap; n-butyllithium; TEA; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; zinc trifluoromethanesulfonate; potassium carbonate; silver nitrate; thiophenol; bis(tri-n-butyltin)oxide; zinc(II) chloride; Lindlar's catalyst; Lindlar catalyst; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; toluene; acetonitrile; 8: Yamaguchi coupling reaction;

DOI:10.1016/S0040-4039(00)02281-4

upstream raw materials:

acetic anhydride

(Z)-(S)-1-[(2R,7R)-7-((S)-1-Benzyloxy-propyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-5-(tetrahydro-pyran-2-yloxy)-pent-3-en-1-ol

2-O-benzyl-3,4-O-isopropylidene-L-threitol

(S)-2-(benzyloxy)-2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl 4-methylbenzenesulfonate

Downstream raw materials:

Acetic acid (Z)-(S)-1-[(2R,7R)-7-((S)-1-benzyloxy-propyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-5-hydroxy-pent-3-enyl ester

(2R,7R)-2-((S)-1-Benzyloxy-propyl)-7-((Z)-(R)-1-chloro-hex-3-en-5-ynyl)-2,3,6,7-tetrahydro-oxepine

(Z)-(S)-1-[(2R,7R)-7-((S)-1-Benzyloxy-propyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-hex-3-en-5-yn-1-ol