(-)-(2R,3R,6S,8S)-Homononactyl-(+)-(2S,3S_.6R,8R)-homononactinsaeure-benzylester

Base Information

• Chemical Name: (-)-(2R,3R,6S,8S)-Homononactyl-(+)-(2S,3S_.6R,8R)-homononactinsaeure-benzylester
• CAS No.: 105210-97-7
• Molecular Formula: C₂₉H₄₄O₇
• Molecular Weight: 504.664
• Mol file: 105210-97-7.mol

Synonyms:(-)-(2R,3R,6S,8S)-Homononactyl-(+)-(2S,3S_.6R,8R)-homononactinsaeure-benzylester

Chemical Property of (-)-(2R,3R,6S,8S)-Homononactyl-(+)-(2S,3S_.6R,8R)-homononactinsaeure-benzylester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(2R,3R,6S,8S)-Homononactyl-(+)-(2S,3S_.6R,8R)-homononactinsaeure-benzylester

There total 14 articles about (-)-(2R,3R,6S,8S)-Homononactyl-(+)-(2S,3S_.6R,8R)-homononactinsaeure-benzylester 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:

(furan-2-yl)ethylene (1487-18-9) → (-)-(2R,3R,6S,8S)-Homononactyl-(+)-(2S,3S.6R,8R)-homononactinsaeure-benzylester (105210-97-7)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) m-tolyl-lithium / 2.) THF, 5 deg C, 4 h, to room temp.

2: 0.5 h

3: 90 percent / TPP, H₂ / 2 / 24 h / 70 °C / 76000 Torr

4: NaClO₂, H₂N-SO₃H, Na₂HPO₄ / dioxane; H₂O / 0.5 h / Ambient temperature

5: KOH / methanol / 0.5 h / Ambient temperature

6: diethyl ether / 0.03 h / Ambient temperature

7: H₂ / 5percent Rh/Al₂O₃ / methanol / 1.5 h / 2280 Torr / Ambient temperature

8: KOH / methanol / 0.5 h / Ambient temperature

9: 1.) KHCO₃ / 1.) H₂O, 2.) DMF, 50 deg C, 1 h

10: 94 percent / Et₃N, DMAP / CH₂Cl₂ / 1 h / 0 °C

11: 1.) KHCO₃ / 1.) H₂O, 2.) DMSO, 50 deg C, 16 h

With dmap; potassium hydroxide; sodium chlorite; disodium hydrogenphosphate; aminosulfonic acid; hydrogen; thiamine diphosphate; m-tolyllithium; potassium hydrogencarbonate; triethylamine; Rh/Al₂O₃; chloro(1,5-cyclooctadiene)rhodium(I) dimer; In 1,4-dioxane; methanol; diethyl ether; dichloromethane; water;

DOI:10.1039/c39860000996

Reference yield:

2-[5-((S)-2-Hydroxy-butyl)-furan-2-yl]-propionic acid → (-)-(2R,3R,6S,8S)-Homononactyl-(+)-(2S,3S.6R,8R)-homononactinsaeure-benzylester (105210-97-7)

Guidance literature:

Multi-step reaction with 6 steps

1: diethyl ether / 0.03 h / Ambient temperature

2: H₂ / 5percent Rh/Al₂O₃ / methanol / 1.5 h / 2280 Torr / Ambient temperature

3: KOH / methanol / 0.5 h / Ambient temperature

4: 1.) KHCO₃ / 1.) H₂O, 2.) DMF, 50 deg C, 1 h

5: 94 percent / Et₃N, DMAP / CH₂Cl₂ / 1 h / 0 °C

6: 1.) KHCO₃ / 1.) H₂O, 2.) DMSO, 50 deg C, 16 h

With dmap; potassium hydroxide; hydrogen; potassium hydrogencarbonate; triethylamine; Rh/Al₂O₃; In methanol; diethyl ether; dichloromethane;

DOI:10.1039/c39860000996

Reference yield:

5-<2(S)-Acetoxybutyl>-α(R,S)-methylfuran-2-acetaldehyd (105210-92-2,105210-93-3) → (-)-(2R,3R,6S,8S)-Homononactyl-(+)-(2S,3S.6R,8R)-homononactinsaeure-benzylester (105210-97-7)

Guidance literature:

Multi-step reaction with 8 steps

1: NaClO₂, H₂N-SO₃H, Na₂HPO₄ / dioxane; H₂O / 0.5 h / Ambient temperature

2: KOH / methanol / 0.5 h / Ambient temperature

3: diethyl ether / 0.03 h / Ambient temperature

4: H₂ / 5percent Rh/Al₂O₃ / methanol / 1.5 h / 2280 Torr / Ambient temperature

5: KOH / methanol / 0.5 h / Ambient temperature

6: 1.) KHCO₃ / 1.) H₂O, 2.) DMF, 50 deg C, 1 h

7: 94 percent / Et₃N, DMAP / CH₂Cl₂ / 1 h / 0 °C

8: 1.) KHCO₃ / 1.) H₂O, 2.) DMSO, 50 deg C, 16 h

With dmap; potassium hydroxide; sodium chlorite; disodium hydrogenphosphate; aminosulfonic acid; hydrogen; potassium hydrogencarbonate; triethylamine; Rh/Al₂O₃; In 1,4-dioxane; methanol; diethyl ether; dichloromethane; water;

DOI:10.1039/c39860000996

upstream raw materials:

(2R,3R,6S,8S)-Homononactinsaeure

(2S,3S,6R,8S)-Homononactinsaeure-benzylester-8-mesylat

(furan-2-yl)ethylene

benzyl bromide

Downstream raw materials:

O-(t-Butyldimethylsilyl)-(-)-(2R,3R,6S,8S)-homononactyl-(+)-(2S,3S_.6R,8R)-homononactyl-(-)-(2R,3R,6S,8S)-homononactyl-(+)-(2S,3S,6R,8R)-homononactinsaeure-benzylester

(-)-(2R,3R,6S,8S)-Homononactyl-(+)-(2S,3S_.6R,8R)-homononactyl-(-)-(2R,3R,6S,8S)-homononactyl-(+)-(2S,3S,6R,8R)-homononactinsaeure-benzylester

Tetranactin

O-(t-Butyldimethylsilyl)-(-)-(2R,3R,6S,8S)-homononactyl-(+)-(2S,3S_.6R,8R)-homononactinsaeure-benzylester