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

Base Information

• Chemical Name: (S)-1-[(2R,7R)-7-((S)-1-Benzyloxy-propyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-5-(tetrahydro-pyran-2-yloxy)-pent-3-yn-1-ol
• CAS No.: 333788-73-1
• Molecular Formula: C₂₆H₃₆O₅
• Molecular Weight: 428.569
• Mol file: 333788-73-1.mol

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

Chemical Property of (S)-1-[(2R,7R)-7-((S)-1-Benzyloxy-propyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-5-(tetrahydro-pyran-2-yloxy)-pent-3-yn-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-[(2R,7R)-7-((S)-1-Benzyloxy-propyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-5-(tetrahydro-pyran-2-yloxy)-pent-3-yn-1-ol

There total 20 articles about (S)-1-[(2R,7R)-7-((S)-1-Benzyloxy-propyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-5-(tetrahydro-pyran-2-yloxy)-pent-3-yn-1-ol 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: 99.0%

3-(tetrahydropyran-2'-yloxy)propyne (6089-04-9) + (2R,7R)-2-((S)-1-Benzyloxy-propyl)-7-(S)-oxiranyl-2,3,6,7-tetrahydro-oxepine (333788-85-5) → (S)-1-[(2R,7R)-7-((S)-1-Benzyloxy-propyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-5-(tetrahydro-pyran-2-yloxy)-pent-3-yn-1-ol (333788-73-1)

Guidance literature:

With n-butyllithium; boron trifluoride diethyl etherate; at -78 ℃;

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

Reference yield:

2-O-benzyl-3,4-O-isopropylidene-L-threitol (84379-53-3) → (S)-1-[(2R,7R)-7-((S)-1-Benzyloxy-propyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-5-(tetrahydro-pyran-2-yloxy)-pent-3-yn-1-ol (333788-73-1)

Guidance literature:

Multi-step reaction with 17 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

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 catalyst; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; 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) → (S)-1-[(2R,7R)-7-((S)-1-Benzyloxy-propyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-5-(tetrahydro-pyran-2-yloxy)-pent-3-yn-1-ol (333788-73-1)

Guidance literature:

Multi-step reaction with 16 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

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 catalyst; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; toluene; acetonitrile; 8: Yamaguchi coupling reaction;

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

upstream raw materials:

3-(tetrahydropyran-2'-yloxy)propyne

(2R,7R)-2-((S)-1-Benzyloxy-propyl)-7-(S)-oxiranyl-2,3,6,7-tetrahydro-oxepine

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:

(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

(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

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