(E)-(4S,7R)-4-(4-Methoxy-benzyloxy)-7-(tetrahydro-pyran-2-yloxy)-oct-2-enoic acid (E)-(1R,2R)-2-(4-methoxy-benzyloxy)-1-methyl-4-[2-(toluene-4-sulfonyl)-ethoxycarbonyl]-but-3-enyl ester

Base Information

Chemical Name:(E)-(4S,7R)-4-(4-Methoxy-benzyloxy)-7-(tetrahydro-pyran-2-yloxy)-oct-2-enoic acid (E)-(1R,2R)-2-(4-methoxy-benzyloxy)-1-methyl-4-[2-(toluene-4-sulfonyl)-ethoxycarbonyl]-but-3-enyl ester
CAS No.:161954-48-9
Molecular Formula:C₄₄H₅₆O₁₂S
Molecular Weight:808.987
Hs Code.:

(E)-(4S,7R)-4-(4-Methoxy-benzyloxy)-7-(tetrahydro-pyran-2-yloxy)-oct-2-enoic acid (E)-(1R,2R)-2-(4-methoxy-benzyloxy)-1-methyl-4-[2-(toluene-4-sulfonyl)-ethoxycarbonyl]-but-3-enyl ester

Synonyms:(E)-(4S,7R)-4-(4-Methoxy-benzyloxy)-7-(tetrahydro-pyran-2-yloxy)-oct-2-enoic acid (E)-(1R,2R)-2-(4-methoxy-benzyloxy)-1-methyl-4-[2-(toluene-4-sulfonyl)-ethoxycarbonyl]-but-3-enyl ester

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Chemical Property of (E)-(4S,7R)-4-(4-Methoxy-benzyloxy)-7-(tetrahydro-pyran-2-yloxy)-oct-2-enoic acid (E)-(1R,2R)-2-(4-methoxy-benzyloxy)-1-methyl-4-[2-(toluene-4-sulfonyl)-ethoxycarbonyl]-but-3-enyl ester

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Technology Process of (E)-(4S,7R)-4-(4-Methoxy-benzyloxy)-7-(tetrahydro-pyran-2-yloxy)-oct-2-enoic acid (E)-(1R,2R)-2-(4-methoxy-benzyloxy)-1-methyl-4-[2-(toluene-4-sulfonyl)-ethoxycarbonyl]-but-3-enyl ester

There total 21 articles about (E)-(4S,7R)-4-(4-Methoxy-benzyloxy)-7-(tetrahydro-pyran-2-yloxy)-oct-2-enoic acid (E)-(1R,2R)-2-(4-methoxy-benzyloxy)-1-methyl-4-[2-(toluene-4-sulfonyl)-ethoxycarbonyl]-but-3-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:

: 36326-38-2,917877-01-1
3-<(4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl>prop-2-enoic acid ethyl ester

: 161954-48-9
(E)-(4S,7R)-4-(4-Methoxy-benzyloxy)-7-(tetrahydro-pyran-2-yloxy)-oct-2-enoic acid (E)-(1R,2R)-2-(4-methoxy-benzyloxy)-1-methyl-4-[2-(toluene-4-sulfonyl)-ethoxycarbonyl]-but-3-enyl ester

Guidance literature:: Multi-step reaction with 16 steps

1: H₂ / Pd-C / ethyl acetate

2: 80 percent / LAH / tetrahydrofuran / 0 °C

3: PDC / CH₂Cl₂ / 40 °C

4: 63 percent / benzene / 80 °C

5: 80 percent / DIBAL-H / CH₂Cl₂

6: 80 percent / TBHP, TIP / (+)DIPT / CH₂Cl₂ / -20 °C

7: 65 percent / Cp₂TiCl₂, Zn, ZnCl₂ / tetrahydrofuran

8: NaH / tetrahydrofuran

9: PTSA / methanol

10: 79 percent / NaH, TsCl / tetrahydrofuran / 0 °C

11: 80 percent / LAH / diethyl ether

12: 95 percent / PTSA / CH₂Cl₂

13: 1.) O₃, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C

14: 80 percent / benzene

15: LiOH / H₂O; tetrahydrofuran

16: 1.) 2,4,6-trichlorobenzoyl chloride, Et₃N,2.) DMAP / 1.) THF, 2.) C₆H₅CH₃, r.t.

With tert.-butylhydroperoxide; dmap; bis(cyclopentadienyl)titanium dichloride; lithium hydroxide; lithium aluminium tetrahydride; dipyridinium dichromate; 2,4,6-trichlorobenzoyl chloride; hydrogen; sodium hydride; diisobutylaluminium hydride; isobutyltriphenylphosphonium bromide; toluene-4-sulfonic acid; ozone; triethylamine; p-toluenesulfonyl chloride; triphenylphosphine; zinc(II) chloride; zinc; palladium on activated charcoal; L-(+)-diisopropyl tartrate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate; benzene;
DOI:10.1016/0040-4039(94)02195-H

Reference yield:

: 36326-39-3
Ethyl 4,5-O-isopropylidene-(S)-4,5-dihydroxypentanoate

: 161954-48-9
(E)-(4S,7R)-4-(4-Methoxy-benzyloxy)-7-(tetrahydro-pyran-2-yloxy)-oct-2-enoic acid (E)-(1R,2R)-2-(4-methoxy-benzyloxy)-1-methyl-4-[2-(toluene-4-sulfonyl)-ethoxycarbonyl]-but-3-enyl ester

Guidance literature:: Multi-step reaction with 15 steps

1: 80 percent / LAH / tetrahydrofuran / 0 °C

2: PDC / CH₂Cl₂ / 40 °C

3: 63 percent / benzene / 80 °C

4: 80 percent / DIBAL-H / CH₂Cl₂

5: 80 percent / TBHP, TIP / (+)DIPT / CH₂Cl₂ / -20 °C

6: 65 percent / Cp₂TiCl₂, Zn, ZnCl₂ / tetrahydrofuran

7: NaH / tetrahydrofuran

8: PTSA / methanol

9: 79 percent / NaH, TsCl / tetrahydrofuran / 0 °C

10: 80 percent / LAH / diethyl ether

11: 95 percent / PTSA / CH₂Cl₂

12: 1.) O₃, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C

13: 80 percent / benzene

14: LiOH / H₂O; tetrahydrofuran

15: 1.) 2,4,6-trichlorobenzoyl chloride, Et₃N,2.) DMAP / 1.) THF, 2.) C₆H₅CH₃, r.t.

With tert.-butylhydroperoxide; dmap; bis(cyclopentadienyl)titanium dichloride; lithium hydroxide; lithium aluminium tetrahydride; dipyridinium dichromate; 2,4,6-trichlorobenzoyl chloride; sodium hydride; diisobutylaluminium hydride; isobutyltriphenylphosphonium bromide; toluene-4-sulfonic acid; ozone; triethylamine; p-toluenesulfonyl chloride; triphenylphosphine; zinc(II) chloride; zinc; L-(+)-diisopropyl tartrate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; benzene;
DOI:10.1016/0040-4039(94)02195-H

Reference yield:

: 51268-87-2
(4S)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)propan-1-ol

: 161954-48-9
(E)-(4S,7R)-4-(4-Methoxy-benzyloxy)-7-(tetrahydro-pyran-2-yloxy)-oct-2-enoic acid (E)-(1R,2R)-2-(4-methoxy-benzyloxy)-1-methyl-4-[2-(toluene-4-sulfonyl)-ethoxycarbonyl]-but-3-enyl ester

Guidance literature:: Multi-step reaction with 14 steps

1: PDC / CH₂Cl₂ / 40 °C

2: 63 percent / benzene / 80 °C

3: 80 percent / DIBAL-H / CH₂Cl₂

4: 80 percent / TBHP, TIP / (+)DIPT / CH₂Cl₂ / -20 °C

5: 65 percent / Cp₂TiCl₂, Zn, ZnCl₂ / tetrahydrofuran

6: NaH / tetrahydrofuran

7: PTSA / methanol

8: 79 percent / NaH, TsCl / tetrahydrofuran / 0 °C

9: 80 percent / LAH / diethyl ether

10: 95 percent / PTSA / CH₂Cl₂

11: 1.) O₃, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C

12: 80 percent / benzene

13: LiOH / H₂O; tetrahydrofuran

14: 1.) 2,4,6-trichlorobenzoyl chloride, Et₃N,2.) DMAP / 1.) THF, 2.) C₆H₅CH₃, r.t.

With tert.-butylhydroperoxide; dmap; bis(cyclopentadienyl)titanium dichloride; lithium hydroxide; lithium aluminium tetrahydride; dipyridinium dichromate; 2,4,6-trichlorobenzoyl chloride; sodium hydride; diisobutylaluminium hydride; isobutyltriphenylphosphonium bromide; toluene-4-sulfonic acid; ozone; triethylamine; p-toluenesulfonyl chloride; triphenylphosphine; zinc(II) chloride; zinc; L-(+)-diisopropyl tartrate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; benzene;
DOI:10.1016/0040-4039(94)02195-H