(1S,5S,6S,8S,10R)-5-{[(2R,3R,4R)-2,3-Dimethyl-4-phenylselanylmethyl-3,4-dihydro-2H-pyran-6-yl]oxoethanamido}-9,9-dimethyl-10-methoxy-8-(prop-2-enyl)-2,4,7-trioxabicyclo[4.4.0]decane

Base Information

• Chemical Name: (1S,5S,6S,8S,10R)-5-{[(2R,3R,4R)-2,3-Dimethyl-4-phenylselanylmethyl-3,4-dihydro-2H-pyran-6-yl]oxoethanamido}-9,9-dimethyl-10-methoxy-8-(prop-2-enyl)-2,4,7-trioxabicyclo[4.4.0]decane
• CAS No.: 218965-70-9
• Molecular Formula: C₂₉H₃₉NO₇Se
• Molecular Weight: 592.591
• Mol file: 218965-70-9.mol

Synonyms:(1S,5S,6S,8S,10R)-5-{[(2R,3R,4R)-2,3-Dimethyl-4-phenylselanylmethyl-3,4-dihydro-2H-pyran-6-yl]oxoethanamido}-9,9-dimethyl-10-methoxy-8-(prop-2-enyl)-2,4,7-trioxabicyclo[4.4.0]decane

Chemical Property of (1S,5S,6S,8S,10R)-5-{[(2R,3R,4R)-2,3-Dimethyl-4-phenylselanylmethyl-3,4-dihydro-2H-pyran-6-yl]oxoethanamido}-9,9-dimethyl-10-methoxy-8-(prop-2-enyl)-2,4,7-trioxabicyclo[4.4.0]decane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,5S,6S,8S,10R)-5-{[(2R,3R,4R)-2,3-Dimethyl-4-phenylselanylmethyl-3,4-dihydro-2H-pyran-6-yl]oxoethanamido}-9,9-dimethyl-10-methoxy-8-(prop-2-enyl)-2,4,7-trioxabicyclo[4.4.0]decane

There total 28 articles about (1S,5S,6S,8S,10R)-5-{[(2R,3R,4R)-2,3-Dimethyl-4-phenylselanylmethyl-3,4-dihydro-2H-pyran-6-yl]oxoethanamido}-9,9-dimethyl-10-methoxy-8-(prop-2-enyl)-2,4,7-trioxabicyclo[4.4.0]decane 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: 78.0%

C14H17LiOSe + (+)-(1S,5R,6S,8R,10S)-10-methoxy-5-{N-(methoxalyl)amino}-9,9-dimethyl-8-(prop-2-enyl)-2,4,7-trioxabicyclo[4.4.0]decane (218965-69-6) → (1S,5S,6S,8S,10R)-5-{[(2R,3R,4R)-2,3-Dimethyl-4-phenylselanylmethyl-3,4-dihydro-2H-pyran-6-yl]oxoethanamido}-9,9-dimethyl-10-methoxy-8-(prop-2-enyl)-2,4,7-trioxabicyclo[4.4.0]decane (218965-70-9)

Guidance literature:

With N,N,N,N,-tetramethylethylenediamine; In tetrahydrofuran; at -78 ℃; for 0.5h;

DOI:10.1055/s-1998-1970

Reference yield:

(2S,3R,4R)-3-benzyloxy-1-tert-butyldiphenylsilyloxy-2,4-methylenedioxypentanal (289666-91-7) → (1S,5S,6S,8S,10R)-5-{[(2R,3R,4R)-2,3-Dimethyl-4-phenylselanylmethyl-3,4-dihydro-2H-pyran-6-yl]oxoethanamido}-9,9-dimethyl-10-methoxy-8-(prop-2-enyl)-2,4,7-trioxabicyclo[4.4.0]decane (218965-70-9)

Guidance literature:

Multi-step reaction with 14 steps

1.1: Yb(OTf)3 / CH₂Cl₂ / 48 h / 20 °C

2.1: NaH / tetrahydrofuran / 0 - 20 °C

2.2: 95 percent / tetrahydrofuran / 0 - 20 °C

3.1: 100 percent / DIBAL-H / tetrahydrofuran / 1 h / 0 °C

4.1: 97 percent / SO₃*Py; Et₃N / dimethylsulfoxide / 2.5 h

5.1: BuLi / tetrahydrofuran; hexane / 0.25 h / 65 °C

5.2: 100 percent / tetrahydrofuran; hexane / 0.33 h / 0 °C

6.1: Li; NH₃ liq. / tetrahydrofuran / 0.33 h / -78 °C

6.2: 74 percent / DDQ / benzene / 3.5 h

7.1: O₃ / methanol / 0.25 h / -78 °C

7.2: Me₂S / methanol / 5 h

8.1: 58.0 mg / pyridine / 16 h

9.1: 17 percent / BF₃*Et₂O; 4 Angstroem molecular sieves / acetonitrile / 0 °C

10.1: Jones reagent / acetone / 0.5 h

11.1: 6.3 mg / Et₃N; (PhO)2PON₃; 4 Angstroem molecular sieves / tetrahydrofuran / 5.5 h / 65 °C

12.1: 78 percent / DMAP; LHMDS / tetrahydrofuran; CH₂Cl₂ / -78 - 0 °C

13.1: 93 percent / TBAF / tetrahydrofuran; CH₂Cl₂ / 0.08 h / 0 °C

14.1: BuLi; TMEDA / tetrahydrofuran / 0.5 h / -78 °C

14.2: tetrahydrofuran / 2.5 h / -78 °C

With pyridine; dmap; n-butyllithium; jones reagent; pyridine-SO₃ complex; N,N,N,N,-tetramethylethylenediamine; 4 A molecular sieve; diphenyl phosphoryl azide; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; ammonia; lithium; sodium hydride; diisobutylaluminium hydride; ozone; triethylamine; lithium hexamethyldisilazane; ytterbium(III) triflate; In tetrahydrofuran; methanol; hexane; dichloromethane; dimethyl sulfoxide; acetone; acetonitrile; 5.2: Wittig reaction / 10.1: Jones oxidation / 11.1: Curtius rearrangement;

DOI:10.1021/jo060803q

Reference yield:

(+)-(2R,3S,4R)-3-benzyloxy-1-tert-butyldiphenylsilyloxy-2,4-methylenedioxypentanol (289666-90-6) → (1S,5S,6S,8S,10R)-5-{[(2R,3R,4R)-2,3-Dimethyl-4-phenylselanylmethyl-3,4-dihydro-2H-pyran-6-yl]oxoethanamido}-9,9-dimethyl-10-methoxy-8-(prop-2-enyl)-2,4,7-trioxabicyclo[4.4.0]decane (218965-70-9)

Guidance literature:

Multi-step reaction with 15 steps

1.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - -30 °C

2.1: Yb(OTf)3 / CH₂Cl₂ / 48 h / 20 °C

3.1: NaH / tetrahydrofuran / 0 - 20 °C

3.2: 95 percent / tetrahydrofuran / 0 - 20 °C

4.1: 100 percent / DIBAL-H / tetrahydrofuran / 1 h / 0 °C

5.1: 97 percent / SO₃*Py; Et₃N / dimethylsulfoxide / 2.5 h

6.1: BuLi / tetrahydrofuran; hexane / 0.25 h / 65 °C

6.2: 100 percent / tetrahydrofuran; hexane / 0.33 h / 0 °C

7.1: Li; NH₃ liq. / tetrahydrofuran / 0.33 h / -78 °C

7.2: 74 percent / DDQ / benzene / 3.5 h

8.1: O₃ / methanol / 0.25 h / -78 °C

8.2: Me₂S / methanol / 5 h

9.1: 58.0 mg / pyridine / 16 h

10.1: 17 percent / BF₃*Et₂O; 4 Angstroem molecular sieves / acetonitrile / 0 °C

11.1: Jones reagent / acetone / 0.5 h

12.1: 6.3 mg / Et₃N; (PhO)2PON₃; 4 Angstroem molecular sieves / tetrahydrofuran / 5.5 h / 65 °C

13.1: 78 percent / DMAP; LHMDS / tetrahydrofuran; CH₂Cl₂ / -78 - 0 °C

14.1: 93 percent / TBAF / tetrahydrofuran; CH₂Cl₂ / 0.08 h / 0 °C

15.1: BuLi; TMEDA / tetrahydrofuran / 0.5 h / -78 °C

15.2: tetrahydrofuran / 2.5 h / -78 °C

With pyridine; dmap; n-butyllithium; jones reagent; oxalyl dichloride; pyridine-SO₃ complex; N,N,N,N,-tetramethylethylenediamine; 4 A molecular sieve; diphenyl phosphoryl azide; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; ammonia; lithium; sodium hydride; diisobutylaluminium hydride; ozone; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; ytterbium(III) triflate; In tetrahydrofuran; methanol; hexane; dichloromethane; dimethyl sulfoxide; acetone; acetonitrile; 1.1: Swern oxidation / 6.2: Wittig reaction / 11.1: Jones oxidation / 12.1: Curtius rearrangement;

DOI:10.1021/jo060803q

upstream raw materials:

(+)-(1S,5R,6S,8R,10S)-10-methoxy-5-{N-(methoxalyl)amino}-9,9-dimethyl-8-(prop-2-enyl)-2,4,7-trioxabicyclo[4.4.0]decane

(4R,5R,6R)-5,6-Dimethyl-4-(phenylselanylmethyl)tetrahydro-2H-pyran-2-one

(+)-(1R,5R,6R,8R,10S)-5-(hydroxy)methyl-10-methoxy-9,9-dimethyl-8-(prop-2-enyl)-2,4,7-trioxabicyclo[4.4.0]decane

(4S,4aS,6R,8S,8aR)-6-Allyl-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine-4-carboxylic acid

Downstream raw materials:

7-O-Benzoyltheopederin D

17-epi-7-O-Benzoyltheopederin D

Benzoic acid (S)-((4S,4aS,6R,8S,8aR)-6-allyl-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl)-((2R,4R,5R,6R)-2-methoxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-methyl ester

Benzoic acid (S)-[(4S,4aS,6R,8S,8aR)-6-(2,5-dihydroxy-pentyl)-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-methyl ester

Refernces

• 1、 Kocienski, Philip,Narquizian, Robert,Raubo, Piotr,Smith, Christopher,Farrugia, Louis J.,Muir, Kenneth,Boyle, F. Thomas. "Synthetic studies on the pederin family of antitumour agents. Syntheses of mycalamide B, theopederin D and pederin". . p. 2357 - 2384. Retrieved 2007/10/03.