2,6-Decadien-8-ynoic acid, 3-methyl-, (2R,4R,6R)-tetrahydro-2-methoxy-2-[(4R)-3-[(4-methoxyphenyl)methyl]- 2-oxo-4-thiazolidinyl]-6-[(3S)-3-methyl-4-hexynyl]-2H-pyran-4-yl ester, (2Z,6E)-

Base Information

• Chemical Name: 2,6-Decadien-8-ynoic acid, 3-methyl-, (2R,4R,6R)-tetrahydro-2-methoxy-2-[(4R)-3-[(4-methoxyphenyl)methyl]- 2-oxo-4-thiazolidinyl]-6-[(3S)-3-methyl-4-hexynyl]-2H-pyran-4-yl ester, (2Z,6E)-
• CAS No.: 861821-49-0
• Molecular Formula: C35H45NO6S
• Molecular Weight: 607.811
• Mol file: 861821-49-0.mol

Synonyms:

Chemical Property of 2,6-Decadien-8-ynoic acid, 3-methyl-, (2R,4R,6R)-tetrahydro-2-methoxy-2-[(4R)-3-[(4-methoxyphenyl)methyl]- 2-oxo-4-thiazolidinyl]-6-[(3S)-3-methyl-4-hexynyl]-2H-pyran-4-yl ester, (2Z,6E)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2,6-Decadien-8-ynoic acid, 3-methyl-, (2R,4R,6R)-tetrahydro-2-methoxy-2-[(4R)-3-[(4-methoxyphenyl)methyl]- 2-oxo-4-thiazolidinyl]-6-[(3S)-3-methyl-4-hexynyl]-2H-pyran-4-yl ester, (2Z,6E)-

There total 15 articles about 2,6-Decadien-8-ynoic acid, 3-methyl-, (2R,4R,6R)-tetrahydro-2-methoxy-2-[(4R)-3-[(4-methoxyphenyl)methyl]- 2-oxo-4-thiazolidinyl]-6-[(3S)-3-methyl-4-hexynyl]-2H-pyran-4-yl ester, (2Z,6E)- 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: 74.0%

Sodium; (2Z,6E)-3-methyl-deca-2,6-dien-8-ynoate + Trifluoro-methanesulfonic acid (2R,4S,6R)-2-methoxy-2-[(R)-3-(4-methoxy-benzyl)-2-oxo-thiazolidin-4-yl]-6-((S)-3-methyl-hex-4-ynyl)-tetrahydro-pyran-4-yl ester (1053714-70-7) → (2Z,6E)-3-Methyl-deca-2,6-dien-8-ynoic acid (2R,4R,6R)-2-methoxy-2-[(R)-3-(4-methoxy-benzyl)-2-oxo-thiazolidin-4-yl]-6-((S)-3-methyl-hex-4-ynyl)-tetrahydro-pyran-4-yl ester (861821-49-0)

Guidance literature:

15-crown-5; In tetrahydrofuran; at 20 ℃; for 24h;

DOI:10.1002/chem.200601135

Reference yield:

(R)-4-[(2R,4S,6R)-4-Hydroxy-2-methoxy-6-((S)-3-methyl-hex-4-ynyl)-tetrahydro-pyran-2-yl]-3-(4-methoxy-benzyl)-thiazolidin-2-one (646994-49-2) → (2Z,6E)-3-Methyl-deca-2,6-dien-8-ynoic acid (2R,4R,6R)-2-methoxy-2-[(R)-3-(4-methoxy-benzyl)-2-oxo-thiazolidin-4-yl]-6-((S)-3-methyl-hex-4-ynyl)-tetrahydro-pyran-4-yl ester (861821-49-0)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / CH₂Cl₂ / 1 h / -20 °C

2: 74 percent / [15]crown-5 ether / tetrahydrofuran / 24 h / 20 °C

With pyridine; 15-crown-5; In tetrahydrofuran; dichloromethane;

DOI:10.1002/chem.200601135

Reference yield:

7,7-dimethoxy-4-methyl-hept-2-yne → (2Z,6E)-3-Methyl-deca-2,6-dien-8-ynoic acid (2R,4R,6R)-2-methoxy-2-[(R)-3-(4-methoxy-benzyl)-2-oxo-thiazolidin-4-yl]-6-((S)-3-methyl-hex-4-ynyl)-tetrahydro-pyran-4-yl ester (861821-49-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: ozone; Sudan red 7B / methanol

1.2: 94 percent / Me₂S / methanol / 24 h / 20 °C

2.1: 75 percent / Ba(OH)2*8H₂O / tetrahydrofuran; H₂O / 3 h

3.1: 57 percent / aq. HCl / tetrahydrofuran / 20 °C

4.1: 92 percent / camphor-10-sulfonic acid / 20 °C

5.1: pyridine / CH₂Cl₂ / 1 h / -20 °C

6.1: 74 percent / [15]crown-5 ether / tetrahydrofuran / 24 h / 20 °C

With pyridine; hydrogenchloride; barium dihydroxide; N-ethyl-1-[{4-(phenylazo)-phenyl}-azo]-2-naphthalenylamine; ozone; 15-crown-5; camphor-10-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1002/chem.200601135

upstream raw materials:

Trifluoro-methanesulfonic acid (2R,4S,6R)-2-methoxy-2-[(R)-3-(4-methoxy-benzyl)-2-oxo-thiazolidin-4-yl]-6-((S)-3-methyl-hex-4-ynyl)-tetrahydro-pyran-4-yl ester

dimethyl 2-((R)-3-(4-methoxybenzyl)-2-oxothiazolidin-4-yl)-2-oxoethyl-phosphonate

(R)-4-[(E)-(5R,8S)-5-(tert-Butyl-dimethyl-silanyloxy)-8-methyl-undec-2-en-9-ynoyl]-3-(4-methoxy-benzyl)-thiazolidin-2-one

4-[2,4-dihydroxy-6-(3-methyl-hex-4-ynyl)-tetrahydro-pyran-2-yl]-3-(4-methoxy-benzyl)-thiazolidin-2-one

Downstream raw materials:

latrunculin A

Refernces

• 1、 Fuerstner, Alois,Turet, Laurent. "Concise and practical synthesis of latrunculin A by ring-closing enyne-yne metathesis". . p. 3462 - 3466. Retrieved 2007/10/03.