(Z)-(2S,8S)-8-Azido-8-[(2S,4R)-2-(4-benzyloxy-butyl)-4-methyl-5-oxo-tetrahydro-furan-2-yl]-2-methyl-oct-4-enoic acid methyl ester

Base Information

• Chemical Name: (Z)-(2S,8S)-8-Azido-8-[(2S,4R)-2-(4-benzyloxy-butyl)-4-methyl-5-oxo-tetrahydro-furan-2-yl]-2-methyl-oct-4-enoic acid methyl ester
• CAS No.: 119243-90-2
• Molecular Formula: C₂₆H₃₇N₃O₅
• Molecular Weight: 471.597
• Mol file: 119243-90-2.mol

Synonyms:(Z)-(2S,8S)-8-Azido-8-[(2S,4R)-2-(4-benzyloxy-butyl)-4-methyl-5-oxo-tetrahydro-furan-2-yl]-2-methyl-oct-4-enoic acid methyl ester

Chemical Property of (Z)-(2S,8S)-8-Azido-8-[(2S,4R)-2-(4-benzyloxy-butyl)-4-methyl-5-oxo-tetrahydro-furan-2-yl]-2-methyl-oct-4-enoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-(2S,8S)-8-Azido-8-[(2S,4R)-2-(4-benzyloxy-butyl)-4-methyl-5-oxo-tetrahydro-furan-2-yl]-2-methyl-oct-4-enoic acid methyl ester

There total 17 articles about (Z)-(2S,8S)-8-Azido-8-[(2S,4R)-2-(4-benzyloxy-butyl)-4-methyl-5-oxo-tetrahydro-furan-2-yl]-2-methyl-oct-4-enoic acid methyl ester 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:

(4-Benzyloxy)butylmagnesium bromide → (Z)-(2S,8S)-8-Azido-8-[(2S,4R)-2-(4-benzyloxy-butyl)-4-methyl-5-oxo-tetrahydro-furan-2-yl]-2-methyl-oct-4-enoic acid methyl ester (119243-90-2)

Guidance literature:

Multi-step reaction with 15 steps

1: 1.) DMS*CuBr, TMEDA / 1.) Et₂O, -78 deg C, 2.) -78 deg C

2: 98 percent / DIBAL / CH₂Cl₂ / -78 °C

3: Ti(O-iPr)4, D-DIPT, t-BuOOH, 4-Angstroem sieves / CH₂Cl₂ / -50 °C

4: ClCOCOCl, DMSO, Et₃N / CH₂Cl₂ / -78 - 0 °C

5: 89 percent / CH₂Cl₂

6: 1.) LiBH₄, MeOH, 2.) H₂ / 2.) 5percent Rh/Al₂O₃ / 1.) Et₂O, 0 deg C, 2.) THF, 1 atm

7: 97 percent / Et₃N / CH₂Cl₂

8: 94 percent / LiN₃, DMPU / 110 °C

9: 81 percent / BF₃*Et₂O / CH₂Cl₂ / 0 °C

10: 97 percent / LiOH / tetrahydrofuran; methanol; H₂O

11: 91 percent / ClCOCOCl, DMSO, Et₃N / CH₂Cl₂ / -78 - 0 °C

12: 81 percent / KO-t-Bu / tetrahydrofuran / -10 °C

13: 72 percent / aq. HBF₄ / methanol / 0.5 h

14: 86 percent / LiOH / tetrahydrofuran; methanol; H₂O / 22 °C

15: 1.) Jones' reagent, Celite / 1.) THF, 0 deg C, 2.) ether

With titanium(IV) isopropylate; methanol; tert.-butylhydroperoxide; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium hydroxide; lithium borohydride; tetrafluoroboric acid; jones' reagent; lithium azide; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; N,N,N,N,-tetramethylethylenediamine; 4 A molecular sieve; Celite; boron trifluoride diethyl etherate; potassium tert-butylate; hydrogen; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; triethylamine; Rh/Al₂O₃; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1021/ja00187a081

Reference yield:

(R)-5-(2-Methoxy-ethoxymethoxy)-4-methyl-pent-1-yne (119243-76-4) → (Z)-(2S,8S)-8-Azido-8-[(2S,4R)-2-(4-benzyloxy-butyl)-4-methyl-5-oxo-tetrahydro-furan-2-yl]-2-methyl-oct-4-enoic acid methyl ester (119243-90-2)

Guidance literature:

Multi-step reaction with 16 steps

1: 1.) n-BuLi / 1.) THF, -78 -> 78 deg C, 2.) -78 deg C

2: 1.) DMS*CuBr, TMEDA / 1.) Et₂O, -78 deg C, 2.) -78 deg C

3: 98 percent / DIBAL / CH₂Cl₂ / -78 °C

4: Ti(O-iPr)4, D-DIPT, t-BuOOH, 4-Angstroem sieves / CH₂Cl₂ / -50 °C

5: ClCOCOCl, DMSO, Et₃N / CH₂Cl₂ / -78 - 0 °C

6: 89 percent / CH₂Cl₂

7: 1.) LiBH₄, MeOH, 2.) H₂ / 2.) 5percent Rh/Al₂O₃ / 1.) Et₂O, 0 deg C, 2.) THF, 1 atm

8: 97 percent / Et₃N / CH₂Cl₂

9: 94 percent / LiN₃, DMPU / 110 °C

10: 81 percent / BF₃*Et₂O / CH₂Cl₂ / 0 °C

11: 97 percent / LiOH / tetrahydrofuran; methanol; H₂O

12: 91 percent / ClCOCOCl, DMSO, Et₃N / CH₂Cl₂ / -78 - 0 °C

13: 81 percent / KO-t-Bu / tetrahydrofuran / -10 °C

14: 72 percent / aq. HBF₄ / methanol / 0.5 h

15: 86 percent / LiOH / tetrahydrofuran; methanol; H₂O / 22 °C

16: 1.) Jones' reagent, Celite / 1.) THF, 0 deg C, 2.) ether

With titanium(IV) isopropylate; methanol; tert.-butylhydroperoxide; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium hydroxide; lithium borohydride; tetrafluoroboric acid; n-butyllithium; jones' reagent; lithium azide; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; N,N,N,N,-tetramethylethylenediamine; 4 A molecular sieve; Celite; boron trifluoride diethyl etherate; potassium tert-butylate; hydrogen; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; triethylamine; Rh/Al₂O₃; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1021/ja00187a081

Reference yield:

(R)-6-(2-Methoxy-ethoxymethoxy)-5-methyl-hex-2-ynoic acid methyl ester (119243-77-5) → (Z)-(2S,8S)-8-Azido-8-[(2S,4R)-2-(4-benzyloxy-butyl)-4-methyl-5-oxo-tetrahydro-furan-2-yl]-2-methyl-oct-4-enoic acid methyl ester (119243-90-2)

Guidance literature:

Multi-step reaction with 15 steps

1: 1.) DMS*CuBr, TMEDA / 1.) Et₂O, -78 deg C, 2.) -78 deg C

2: 98 percent / DIBAL / CH₂Cl₂ / -78 °C

3: Ti(O-iPr)4, D-DIPT, t-BuOOH, 4-Angstroem sieves / CH₂Cl₂ / -50 °C

4: ClCOCOCl, DMSO, Et₃N / CH₂Cl₂ / -78 - 0 °C

5: 89 percent / CH₂Cl₂

6: 1.) LiBH₄, MeOH, 2.) H₂ / 2.) 5percent Rh/Al₂O₃ / 1.) Et₂O, 0 deg C, 2.) THF, 1 atm

7: 97 percent / Et₃N / CH₂Cl₂

8: 94 percent / LiN₃, DMPU / 110 °C

9: 81 percent / BF₃*Et₂O / CH₂Cl₂ / 0 °C

10: 97 percent / LiOH / tetrahydrofuran; methanol; H₂O

11: 91 percent / ClCOCOCl, DMSO, Et₃N / CH₂Cl₂ / -78 - 0 °C

12: 81 percent / KO-t-Bu / tetrahydrofuran / -10 °C

13: 72 percent / aq. HBF₄ / methanol / 0.5 h

14: 86 percent / LiOH / tetrahydrofuran; methanol; H₂O / 22 °C

15: 1.) Jones' reagent, Celite / 1.) THF, 0 deg C, 2.) ether

With titanium(IV) isopropylate; methanol; tert.-butylhydroperoxide; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium hydroxide; lithium borohydride; tetrafluoroboric acid; jones' reagent; lithium azide; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; N,N,N,N,-tetramethylethylenediamine; 4 A molecular sieve; Celite; boron trifluoride diethyl etherate; potassium tert-butylate; hydrogen; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; triethylamine; Rh/Al₂O₃; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1021/ja00187a081

upstream raw materials:

diazomethane

(Z)-(2R,4S,5S,11S)-5-Azido-4-(4-benzyloxy-butyl)-2,11-dimethyl-dodec-8-ene-1,4,12-triol

(R)-5-(2-Methoxy-ethoxymethoxy)-4-methyl-pent-1-yne

(R)-6-(2-Methoxy-ethoxymethoxy)-5-methyl-hex-2-ynoic acid methyl ester

Downstream raw materials:

croomine