(S,Z)-1-((2S,3S)-3-(benzyloxy)-6-oxo-3,6-dihydro-2H-pyran-2-yl)hept-1-en-3-yl acetate

Base Information

• Chemical Name: (S,Z)-1-((2S,3S)-3-(benzyloxy)-6-oxo-3,6-dihydro-2H-pyran-2-yl)hept-1-en-3-yl acetate
• CAS No.: 1422040-32-1
• Molecular Formula: C₂₁H₂₆O₅
• Molecular Weight: 358.434
• Mol file: 1422040-32-1.mol

Synonyms:(S,Z)-1-((2S,3S)-3-(benzyloxy)-6-oxo-3,6-dihydro-2H-pyran-2-yl)hept-1-en-3-yl acetate

Chemical Property of (S,Z)-1-((2S,3S)-3-(benzyloxy)-6-oxo-3,6-dihydro-2H-pyran-2-yl)hept-1-en-3-yl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S,Z)-1-((2S,3S)-3-(benzyloxy)-6-oxo-3,6-dihydro-2H-pyran-2-yl)hept-1-en-3-yl acetate

There total 58 articles about (S,Z)-1-((2S,3S)-3-(benzyloxy)-6-oxo-3,6-dihydro-2H-pyran-2-yl)hept-1-en-3-yl acetate 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%

(5S,6S)-5-(benzyloxy)-6-((S,Z)-3-hydroxyhept-1-enyl)-5,6-dihydro-2H-pyran-2-one (1422040-31-0) + acetic anhydride (108-24-7) → (S,Z)-1-((2S,3S)-3-(benzyloxy)-6-oxo-3,6-dihydro-2H-pyran-2-yl)hept-1-en-3-yl acetate (1422040-32-1)

Guidance literature:

With pyridine; at 0 - 20 ℃; for 2h;

DOI:10.1016/j.tetasy.2014.09.009

Reference yield:

(5S,6S)-5-(benzyloxy)-6-((S)-3-hydroxyhept-1-ynyl)-5,6-dihydro-2H-pyran-2-one (1422040-30-9) → (S,Z)-1-((2S,3S)-3-(benzyloxy)-6-oxo-3,6-dihydro-2H-pyran-2-yl)hept-1-en-3-yl acetate (1422040-32-1)

Guidance literature:

Multi-step reaction with 2 steps

1: quinoline; hydrogen / ethyl acetate / 20 °C / 760.05 Torr

2: triethylamine; dmap / dichloromethane / 1 h / 0 - 20 °C

With quinoline; dmap; hydrogen; triethylamine; In dichloromethane; ethyl acetate;

DOI:10.1016/j.tetlet.2012.12.039

Reference yield:

tert-butyldimethyl{(S)-1-[(S)-oxiran-2-yl]prop-2-ynyloxy}silane → (S,Z)-1-((2S,3S)-3-(benzyloxy)-6-oxo-3,6-dihydro-2H-pyran-2-yl)hept-1-en-3-yl acetate (1422040-32-1)

Guidance literature:

Multi-step reaction with 12 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.83 h / -20 °C

1.2: 3 h / -20 - 20 °C

2.1: sodium hydride; tetra-(n-butyl)ammonium iodide / tetrahydrofuran / 8 h / 0 - 20 °C

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

3.2: 4 h / -78 - 20 °C / Inert atmosphere

4.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane; dimethyl sulfoxide / 2 h / 0 - 20 °C

5.1: triethylamine; formic acid; Noyori's catalyst / dichloromethane / 20 °C

6.1: 1H-imidazole / dichloromethane / 1 h / 0 °C

7.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; toluene; acetone / 24 h / 20 °C

8.1: sodium periodate / tetrahydrofuran; water / 0.5 h / 0 °C

9.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

9.2: 0.67 h / -78 °C / Inert atmosphere

10.1: toluene-4-sulfonic acid / dichloromethane / 3 h / 20 °C

11.1: 5% Pd-CaCO3; lead acetate; quinoline; hydrogen / ethyl acetate / 20 °C / 760.05 Torr

12.1: triethylamine; dmap / dichloromethane / 1 h / 0 °C

With 1H-imidazole; quinoline; dmap; sodium periodate; osmium(VIII) oxide; Noyori's catalyst; n-butyllithium; formic acid; 5% Pd-CaCO3; hydrogen; lead acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; hexane; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; acetone; toluene; 5.1: |Noyori Asymmetric Hydrogenation / 9.2: |Still-Gennary Z-Olefination;

DOI:10.1055/s-0034-1378912

upstream raw materials:

(4S,5S,9S)-4-(benzyloxy)-7,7-diisopropyl-1-(4-methoxyphenyl)-5,9-divinyl-2,6,8-trioxa-7-silatridecane

(2S,3S)-2-(benzyloxy)-3-(((S)-hept-1-en-3-yloxy)diisopropylsilyloxy)pent-4-en-1-ol

(S)-2-(benzyloxy)-2-((4S,7S)-7-butyl-2,2-diisopropyl-4,7-dihydro-1,3,2-dioxasilepin-4-yl)ethanol

(S,Z)-methyl 4-(benzyloxy)-4-((4S,7S)-7-butyl-2,2-diisopropyl-4,7-dihydro-1,3,2-ioxasilepin-4-yl)but-2-enoate

Refernces

• 1、 Sabitha, Gowravaram,Ankireddy, Praveen,Das, Sukant Kishore. "The first total synthesis of pectinolides D and e and total synthesis of pectinolides A and C". . p. 330 - 342. Retrieved 2015/02/19.
• 2、 Kumar, T. Vijaya,Shankaraiah,Babu, K. Suresh,Rao, J. Madhusudana. "Stereoselective synthesis of pectinolide C". . p. 1397 - 1400. Retrieved 2013/04/10.