Benzoic acid (2S,3S,4R,5R,6S)-6-[(2R,3S,4R,5S,6S)-5-hydroxy-3-(4-methoxy-benzyloxy)-4-methyl-6-vinyl-tetrahydro-pyran-2-ylmethyl]-5-(4-methoxy-benzyloxy)-4-methyl-2-vinyl-tetrahydro-pyran-3-yl ester

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Chemical Name:Benzoic acid (2S,3S,4R,5R,6S)-6-[(2R,3S,4R,5S,6S)-5-hydroxy-3-(4-methoxy-benzyloxy)-4-methyl-6-vinyl-tetrahydro-pyran-2-ylmethyl]-5-(4-methoxy-benzyloxy)-4-methyl-2-vinyl-tetrahydro-pyran-3-yl ester
CAS No.:846577-28-4
Molecular Formula:C₄₀H₄₈O₉
Molecular Weight:672.816
Hs Code.:

Benzoic acid (2S,3S,4R,5R,6S)-6-[(2R,3S,4R,5S,6S)-5-hydroxy-3-(4-methoxy-benzyloxy)-4-methyl-6-vinyl-tetrahydro-pyran-2-ylmethyl]-5-(4-methoxy-benzyloxy)-4-methyl-2-vinyl-tetrahydro-pyran-3-yl ester

Synonyms:Benzoic acid (2S,3S,4R,5R,6S)-6-[(2R,3S,4R,5S,6S)-5-hydroxy-3-(4-methoxy-benzyloxy)-4-methyl-6-vinyl-tetrahydro-pyran-2-ylmethyl]-5-(4-methoxy-benzyloxy)-4-methyl-2-vinyl-tetrahydro-pyran-3-yl ester

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Chemical Property of Benzoic acid (2S,3S,4R,5R,6S)-6-[(2R,3S,4R,5S,6S)-5-hydroxy-3-(4-methoxy-benzyloxy)-4-methyl-6-vinyl-tetrahydro-pyran-2-ylmethyl]-5-(4-methoxy-benzyloxy)-4-methyl-2-vinyl-tetrahydro-pyran-3-yl ester

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Technology Process of Benzoic acid (2S,3S,4R,5R,6S)-6-[(2R,3S,4R,5S,6S)-5-hydroxy-3-(4-methoxy-benzyloxy)-4-methyl-6-vinyl-tetrahydro-pyran-2-ylmethyl]-5-(4-methoxy-benzyloxy)-4-methyl-2-vinyl-tetrahydro-pyran-3-yl ester

There total 17 articles about Benzoic acid (2S,3S,4R,5R,6S)-6-[(2R,3S,4R,5S,6S)-5-hydroxy-3-(4-methoxy-benzyloxy)-4-methyl-6-vinyl-tetrahydro-pyran-2-ylmethyl]-5-(4-methoxy-benzyloxy)-4-methyl-2-vinyl-tetrahydro-pyran-3-yl 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: 83.0%

: 846577-17-1
C₃₃H₄₄O₈

: 65-85-0,8013-63-6
benzoic acid

: 846577-28-4
Benzoic acid (2S,3S,4R,5R,6S)-6-[(2R,3S,4R,5S,6S)-5-hydroxy-3-(4-methoxy-benzyloxy)-4-methyl-6-vinyl-tetrahydro-pyran-2-ylmethyl]-5-(4-methoxy-benzyloxy)-4-methyl-2-vinyl-tetrahydro-pyran-3-yl ester

Guidance literature:: With dmap; dacarbazine; In dichloromethane; at 20 ℃; for 24h;
DOI:10.1021/ol0473400

Reference yield:

: (2S,4R)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-pentanedial

: 846577-28-4
Benzoic acid (2S,3S,4R,5R,6S)-6-[(2R,3S,4R,5S,6S)-5-hydroxy-3-(4-methoxy-benzyloxy)-4-methyl-6-vinyl-tetrahydro-pyran-2-ylmethyl]-5-(4-methoxy-benzyloxy)-4-methyl-2-vinyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 16 steps

1.1: KHMDS; 18-C-6 / tetrahydrofuran / 0.25 h / -78 °C

1.2: 6.3 g / tetrahydrofuran / -78 - 20 °C

2.1: 100 percent / DIBAL / CH₂Cl₂; hexane / 1 h / -78 °C

3.1: BH₃*THF / tetrahydrofuran / 0.75 h

3.2: 70 percent / NaBO₃*H₂O / tetrahydrofuran; H₂O / 1 h / 20 °C

4.1: PPTS / CH₂Cl₂ / 20 °C

5.1: 2.03 g / DIBAL / toluene / -78 - 0 °C

6.1: 97 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 0.5 h / -78 - 20 °C

7.1: NaH / tetrahydrofuran / -78 °C

7.2: 96 percent / tetrahydrofuran / -78 - 20 °C

8.1: 97 percent / DIBAL / CH₂Cl₂; hexane / 1 h / -78 °C

9.1: 68 percent / Ti(OiPr)4; L-(+)-DET; tert-butyl hydroperoxide / CH₂Cl₂; decane / -20 °C

10.1: 94 percent / Et₃N / CH₂Cl₂ / 1 h / 20 °C

11.1: NaI / butan-2-one / 2 h / Heating

12.1: 1.12 g / Zn / I₂ / methanol / 0.5 h / Heating

13.1: 80 percent / [(benzylidene)(1,3-dimesitylimidazolidin-2-yl)(PCy₃)RuCl₂] / CH₂Cl₂ / 20 °C

14.1: 89 percent / TBAF / tetrahydrofuran / 20 °C

15.1: 76 percent / Pd₂(dba)3*CHCl₃; (R,R)-DPPBA / CH₂Cl₂ / 20 °C

16.1: 83 percent / DMAP; DIC / CH₂Cl₂ / 24 h / 20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; borane-THF; oxalyl dichloride; 18-crown-6 ether; diethyl (2R,3R)-tartrate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; dacarbazine; triethylamine; sodium iodide; zinc; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; (R,R)-DPPBA; iodine; In tetrahydrofuran; methanol; decane; hexane; dichloromethane; toluene; butanone; 6.1: Swern oxidation / 7.2: Horner-Wadsworth-Emmons reaction / 9.1: Sharpless asymmetric epoxidation;
DOI:10.1021/ol0473400

Reference yield:

: 846577-21-7
(2Z,7Z)-(4S,6R)-4,6-Bis-(tert-butyl-dimethyl-silanyloxy)-2,8-dimethyl-nona-2,7-diene-1,9-diol

: 846577-28-4
Benzoic acid (2S,3S,4R,5R,6S)-6-[(2R,3S,4R,5S,6S)-5-hydroxy-3-(4-methoxy-benzyloxy)-4-methyl-6-vinyl-tetrahydro-pyran-2-ylmethyl]-5-(4-methoxy-benzyloxy)-4-methyl-2-vinyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 14 steps

1.1: BH₃*THF / tetrahydrofuran / 0.75 h

1.2: 70 percent / NaBO₃*H₂O / tetrahydrofuran; H₂O / 1 h / 20 °C

2.1: PPTS / CH₂Cl₂ / 20 °C

3.1: 2.03 g / DIBAL / toluene / -78 - 0 °C

4.1: 97 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 0.5 h / -78 - 20 °C

5.1: NaH / tetrahydrofuran / -78 °C

5.2: 96 percent / tetrahydrofuran / -78 - 20 °C

6.1: 97 percent / DIBAL / CH₂Cl₂; hexane / 1 h / -78 °C

7.1: 68 percent / Ti(OiPr)4; L-(+)-DET; tert-butyl hydroperoxide / CH₂Cl₂; decane / -20 °C

8.1: 94 percent / Et₃N / CH₂Cl₂ / 1 h / 20 °C

9.1: NaI / butan-2-one / 2 h / Heating

10.1: 1.12 g / Zn / I₂ / methanol / 0.5 h / Heating

11.1: 80 percent / [(benzylidene)(1,3-dimesitylimidazolidin-2-yl)(PCy₃)RuCl₂] / CH₂Cl₂ / 20 °C

12.1: 89 percent / TBAF / tetrahydrofuran / 20 °C

13.1: 76 percent / Pd₂(dba)3*CHCl₃; (R,R)-DPPBA / CH₂Cl₂ / 20 °C

14.1: 83 percent / DMAP; DIC / CH₂Cl₂ / 24 h / 20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; borane-THF; oxalyl dichloride; diethyl (2R,3R)-tartrate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; dacarbazine; triethylamine; sodium iodide; zinc; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; (R,R)-DPPBA; iodine; In tetrahydrofuran; methanol; decane; hexane; dichloromethane; toluene; butanone; 4.1: Swern oxidation / 5.2: Horner-Wadsworth-Emmons reaction / 7.1: Sharpless asymmetric epoxidation;
DOI:10.1021/ol0473400