{2-[(E)-(4R,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-8-phenyl-oct-7-enyl]-[1,3]dithian-2-yl}-((4R,5R,4'S,5'R)-4,4',5'-tris-benzyloxymethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methanol

Base Information

• Chemical Name: {2-[(E)-(4R,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-8-phenyl-oct-7-enyl]-[1,3]dithian-2-yl}-((4R,5R,4'S,5'R)-4,4',5'-tris-benzyloxymethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methanol
• CAS No.: 528865-13-6
• Molecular Formula: C₇₀H₈₈O₉S₂Si
• Molecular Weight: 1165.68

Synonyms:

Chemical Property of {2-[(E)-(4R,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-8-phenyl-oct-7-enyl]-[1,3]dithian-2-yl}-((4R,5R,4'S,5'R)-4,4',5'-tris-benzyloxymethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methanol

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of {2-[(E)-(4R,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-8-phenyl-oct-7-enyl]-[1,3]dithian-2-yl}-((4R,5R,4'S,5'R)-4,4',5'-tris-benzyloxymethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methanol

There total 15 articles about {2-[(E)-(4R,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-8-phenyl-oct-7-enyl]-[1,3]dithian-2-yl}-((4R,5R,4'S,5'R)-4,4',5'-tris-benzyloxymethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methanol 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:

(2S,3R,4S,5R)-2,3,4,5-bis(di-O-isopropylidene)-6-benzyloxy-(3,4-bis(benzyloxymethyl))hexan-1-al (172790-40-8) + tert-Butyl-{(E)-(1R,2R)-2-methyl-1-[3-(1-oxo-1λ4-[1,3]dithian-2-yl)-propyl]-5-phenyl-pent-4-enyloxy}-diphenyl-silane → {2-[(E)-(4R,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-8-phenyl-oct-7-enyl]-[1,3]dithian-2-yl}-((4R,5R,4'S,5'R)-4,4',5'-tris-benzyloxymethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methanol (528865-13-6)

Guidance literature:

tert-Butyl-{(E)-(1R,2R)-2-methyl-1-[3-(1-oxo-1λ⁴-[1,3]dithian-2-yl)-propyl]-5-phenyl-pent-4-enyloxy}-diphenyl-silane; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.25h;

(2S,3R,4S,5R)-2,3,4,5-bis(di-O-isopropylidene)-6-benzyloxy-(3,4-bis(benzyloxymethyl))hexan-1-al; In tetrahydrofuran; hexane; at -78 ℃; for 1.16667h;

With diphosphorus tetraiodide; triethylamine; In dichloromethane; at 20 ℃; for 0.666667h;

DOI:10.1016/S0040-4020(02)01514-4

Reference yield:

5-benzyloxy-1-pentanal (78999-24-3) → {2-[(E)-(4R,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-8-phenyl-oct-7-enyl]-[1,3]dithian-2-yl}-((4R,5R,4'S,5'R)-4,4',5'-tris-benzyloxymethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methanol (528865-13-6)

Guidance literature:

Multi-step reaction with 13 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

With pyridine; 1H-imidazole; lithium borohydride; n-butyllithium; boron trichloride - methyl sulfide complex; di-n-butylboryl trifluoromethanesulfonate; sulfuric acid; boron trifluoride diethyl etherate; 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:

(4S,2'R,3'R)-3-(7'-benzyloxy-3'-hydroxy-2'-methylheptanoyl)-4-isopropyl-1,3-oxazolidin-2-one (528864-90-6) → {2-[(E)-(4R,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-8-phenyl-oct-7-enyl]-[1,3]dithian-2-yl}-((4R,5R,4'S,5'R)-4,4',5'-tris-benzyloxymethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methanol (528865-13-6)

Guidance literature:

Multi-step reaction with 12 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

With pyridine; 1H-imidazole; lithium borohydride; n-butyllithium; boron trichloride - methyl sulfide complex; sulfuric acid; boron trifluoride diethyl etherate; 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

upstream raw materials:

(2S,3R,4S,5R)-2,3,4,5-bis(di-O-isopropylidene)-6-benzyloxy-(3,4-bis(benzyloxymethyl))hexan-1-al

Benzyl phenyl sulfone

O,O-diethyl benzylphosphonate

5-benzyloxy-1-pentanal

Downstream raw materials:

(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

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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