Acetic acid (E)-(1R,2R)-1-(3-{2-[(R)-hydroxy-((4R,5R,4'S,5'R)-4,4',5'-tris-benzyloxymethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methyl]-[1,3]dithian-2-yl}-propyl)-2-methyl-5-phenyl-pent-4-enyl ester

Base Information

Chemical Name:Acetic acid (E)-(1R,2R)-1-(3-{2-[(R)-hydroxy-((4R,5R,4'S,5'R)-4,4',5'-tris-benzyloxymethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methyl]-[1,3]dithian-2-yl}-propyl)-2-methyl-5-phenyl-pent-4-enyl ester
CAS No.:528865-17-0
Molecular Formula:C₅₆H₇₂O₁₀S₂
Molecular Weight:969.314
Hs Code.:

Acetic acid (E)-(1R,2R)-1-(3-{2-[(R)-hydroxy-((4R,5R,4'S,5'R)-4,4',5'-tris-benzyloxymethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methyl]-[1,3]dithian-2-yl}-propyl)-2-methyl-5-phenyl-pent-4-enyl ester

Synonyms:Acetic acid (E)-(1R,2R)-1-(3-{2-[(R)-hydroxy-((4R,5R,4'S,5'R)-4,4',5'-tris-benzyloxymethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methyl]-[1,3]dithian-2-yl}-propyl)-2-methyl-5-phenyl-pent-4-enyl ester

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Chemical Property of Acetic acid (E)-(1R,2R)-1-(3-{2-[(R)-hydroxy-((4R,5R,4'S,5'R)-4,4',5'-tris-benzyloxymethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methyl]-[1,3]dithian-2-yl}-propyl)-2-methyl-5-phenyl-pent-4-enyl ester

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Technology Process of Acetic acid (E)-(1R,2R)-1-(3-{2-[(R)-hydroxy-((4R,5R,4'S,5'R)-4,4',5'-tris-benzyloxymethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methyl]-[1,3]dithian-2-yl}-propyl)-2-methyl-5-phenyl-pent-4-enyl ester

There total 17 articles about Acetic acid (E)-(1R,2R)-1-(3-{2-[(R)-hydroxy-((4R,5R,4'S,5'R)-4,4',5'-tris-benzyloxymethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methyl]-[1,3]dithian-2-yl}-propyl)-2-methyl-5-phenyl-pent-4-enyl 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: 69.0%

: 108-24-7
acetic anhydride

: 528865-16-9
(E)-(4R,5R)-1-{2-[(R)-Hydroxy-((4R,5R,4'S,5'R)-4,4',5'-tris-benzyloxymethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methyl]-[1,3]dithian-2-yl}-5-methyl-8-phenyl-oct-7-en-4-ol

: 528865-17-0
Acetic acid (E)-(1R,2R)-1-(3-{2-[(R)-hydroxy-((4R,5R,4'S,5'R)-4,4',5'-tris-benzyloxymethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methyl]-[1,3]dithian-2-yl}-propyl)-2-methyl-5-phenyl-pent-4-enyl ester

Guidance literature:: With pyridine; dmap; at 60 ℃; for 3h;
DOI:10.1016/S0040-4020(02)01514-4

Reference yield:

: 78999-24-3
5-benzyloxy-1-pentanal

: 528865-17-0
Acetic acid (E)-(1R,2R)-1-(3-{2-[(R)-hydroxy-((4R,5R,4'S,5'R)-4,4',5'-tris-benzyloxymethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methyl]-[1,3]dithian-2-yl}-propyl)-2-methyl-5-phenyl-pent-4-enyl ester

Guidance literature:: Multi-step reaction with 15 steps

1.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / -78 - 0 °C

1.2: CH₂Cl₂ / -78 - 20 °C

1.3: 88 percent / aq. H₂O₂ / methanol; CH₂Cl₂; aq. phosphate buffer / 0 - 20 °C

2.1: 81 percent / imidazole / dimethylformamide / 23 h

3.1: 62 percent / LiBH₄ / tetrahydrofuran; methanol / 0 - 20 °C

4.1: 89 percent / pyridine / CH₂Cl₂ / 24 h

5.1: 98 percent / dimethylsulfoxide / 20 h / 60 °C

6.1: DIBAL-H / CH₂Cl₂ / 1.58 h / -78 °C

7.1: 14.5 g / aq. H₂SO₄; aq. NH₄Cl / 0.33 h / 20 °C

8.1: 95 percent / BCl₃*SMe₂ / CH₂Cl₂ / 1.5 h

9.1: 94 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.08 h

10.1: 100 percent / BF₃*OEt₂ / CH₂Cl₂ / 12 h

11.1: 44 percent / mCPBA / CH₂Cl₂ / 0.08 h / 0 °C

12.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

12.2: tetrahydrofuran; hexane / 1.17 h / -78 °C

12.3: 2.04 g / P₂I₄; Et₃N / CH₂Cl₂ / 0.67 h / 20 °C

13.1: 194 mg / TBAF / tetrahydrofuran / 25 h / 80 °C

14.1: 69 percent / DMAP; pyridine / 3 h / 60 °C

With pyridine; 1H-imidazole; dmap; lithium borohydride; n-butyllithium; boron trichloride - methyl sulfide complex; di-n-butylboryl trifluoromethanesulfonate; sulfuric acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; ammonium chloride; Dess-Martin periodane; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 8.1: Julia olefination;
DOI:10.1016/S0040-4020(02)01514-4

Reference yield:

: 528864-90-6
(4S,2'R,3'R)-3-(7'-benzyloxy-3'-hydroxy-2'-methylheptanoyl)-4-isopropyl-1,3-oxazolidin-2-one

: 528865-17-0
Acetic acid (E)-(1R,2R)-1-(3-{2-[(R)-hydroxy-((4R,5R,4'S,5'R)-4,4',5'-tris-benzyloxymethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methyl]-[1,3]dithian-2-yl}-propyl)-2-methyl-5-phenyl-pent-4-enyl ester

Guidance literature:: Multi-step reaction with 14 steps

1.1: 81 percent / imidazole / dimethylformamide / 23 h

2.1: 62 percent / LiBH₄ / tetrahydrofuran; methanol / 0 - 20 °C

3.1: 89 percent / pyridine / CH₂Cl₂ / 24 h

4.1: 98 percent / dimethylsulfoxide / 20 h / 60 °C

5.1: DIBAL-H / CH₂Cl₂ / 1.58 h / -78 °C

6.1: 14.5 g / aq. H₂SO₄; aq. NH₄Cl / 0.33 h / 20 °C

7.1: 95 percent / BCl₃*SMe₂ / CH₂Cl₂ / 1.5 h

8.1: 94 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.08 h

9.1: 100 percent / BF₃*OEt₂ / CH₂Cl₂ / 12 h

10.1: 44 percent / mCPBA / CH₂Cl₂ / 0.08 h / 0 °C

11.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

11.2: tetrahydrofuran; hexane / 1.17 h / -78 °C

11.3: 2.04 g / P₂I₄; Et₃N / CH₂Cl₂ / 0.67 h / 20 °C

12.1: 194 mg / TBAF / tetrahydrofuran / 25 h / 80 °C

13.1: 69 percent / DMAP; pyridine / 3 h / 60 °C

With pyridine; 1H-imidazole; dmap; lithium borohydride; n-butyllithium; boron trichloride - methyl sulfide complex; sulfuric acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; ammonium chloride; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 7.1: Julia olefination;
DOI:10.1016/S0040-4020(02)01514-4