2-[(2S,3S,4S,5R)-4-Benzyloxy-2-[(E)-10-(4-methoxy-benzyloxy)-dec-2-enyl]-5-(2-methyl-[1,3]dioxolan-2-ylmethyl)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

Base Information

Chemical Name:2-[(2S,3S,4S,5R)-4-Benzyloxy-2-[(E)-10-(4-methoxy-benzyloxy)-dec-2-enyl]-5-(2-methyl-[1,3]dioxolan-2-ylmethyl)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione
CAS No.:163041-05-2
Molecular Formula:C₄₃H₅₃NO₈
Molecular Weight:711.896
Hs Code.:

Synonyms:2-[(2S,3S,4S,5R)-4-Benzyloxy-2-[(E)-10-(4-methoxy-benzyloxy)-dec-2-enyl]-5-(2-methyl-[1,3]dioxolan-2-ylmethyl)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

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Chemical Property of 2-[(2S,3S,4S,5R)-4-Benzyloxy-2-[(E)-10-(4-methoxy-benzyloxy)-dec-2-enyl]-5-(2-methyl-[1,3]dioxolan-2-ylmethyl)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

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Technology Process of 2-[(2S,3S,4S,5R)-4-Benzyloxy-2-[(E)-10-(4-methoxy-benzyloxy)-dec-2-enyl]-5-(2-methyl-[1,3]dioxolan-2-ylmethyl)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

There total 13 articles about 2-[(2S,3S,4S,5R)-4-Benzyloxy-2-[(E)-10-(4-methoxy-benzyloxy)-dec-2-enyl]-5-(2-methyl-[1,3]dioxolan-2-ylmethyl)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione 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:

: 131522-45-7
(1S,2S,3S,4S,5R)-2-(2-Methyl-2-propenyl)-3,4-epoxy-6,8-dioxabicyclo<3.2.1>octan-3-ol

: 163041-05-2
2-[(2S,3S,4S,5R)-4-Benzyloxy-2-[(E)-10-(4-methoxy-benzyloxy)-dec-2-enyl]-5-(2-methyl-[1,3]dioxolan-2-ylmethyl)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

Guidance literature:: Multi-step reaction with 12 steps

1: NaN₃, n-tetrabutylammonium iodide / 1,2-dimethoxy-ethane; 2-methoxy-ethanol; H₂O / 72 h / 120 °C

2: 1.) NaH, imidazole, 2.) n-tetrabutylammonium iodide / 1.) THF, DMF, 0 deg C, 2.) r.t., 4 h

3: H₂ / Lindlar catalyst / ethanol / 24 h / 760 Torr / Ambient temperature

4: 1.) pyridine, 2.) Ac₂O / 1.) 90 deg C, 1 h, 2.) 90 deg C, 2 h

5: 87 percent / BF₃*Et₂O / 0.08 h / Ambient temperature

6: 85 percent / TMSOTf / acetonitrile / 8 h / -20 °C

7: 1.) O₃, 2.) Me₂S / 1.) MeOH, CH₂Cl₂, -78 deg C, 15 min

8: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 20 min, 2.) THF, 5 min

9: 79 percent / camphorsulfonic acid, triethyl orthoformate / benzene / 168 h / Ambient temperature

10: DBU / methanol / 5 h / Ambient temperature

11: Dess-Martin periodinane, 4 Angstroem molecular sieves / CH₂Cl₂ / 10 h / Ambient temperature

12: (Ph₃P)3RhCl / xylene / 0.75 h / Heating

With pyridine; 1H-imidazole; Wilkinson's catalyst; n-butyllithium; sodium azide; dimethylsulfide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; hydrogen; acetic anhydride; tetra-(n-butyl)ammonium iodide; sodium hydride; Dess-Martin periodane; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; orthoformic acid triethyl ester; Lindlar's catalyst; In methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; 2-methoxy-ethanol; water; acetonitrile; xylene; benzene;
DOI:10.1021/jo00112a040

Reference yield:

: 110104-41-1
(1S,2S,3S,4R,5R)-2-(2-Methyl-2-propenyl)-4-(p-toluenesulfonyl)oxy-6,8-dioxabicyclo<3.2.1>octan-3-ol

: 163041-05-2
2-[(2S,3S,4S,5R)-4-Benzyloxy-2-[(E)-10-(4-methoxy-benzyloxy)-dec-2-enyl]-5-(2-methyl-[1,3]dioxolan-2-ylmethyl)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

Guidance literature:: Multi-step reaction with 13 steps

1: NaH, imidazole / tetrahydrofuran / 0.5 h / 0 °C

2: NaN₃, n-tetrabutylammonium iodide / 1,2-dimethoxy-ethane; 2-methoxy-ethanol; H₂O / 72 h / 120 °C

3: 1.) NaH, imidazole, 2.) n-tetrabutylammonium iodide / 1.) THF, DMF, 0 deg C, 2.) r.t., 4 h

4: H₂ / Lindlar catalyst / ethanol / 24 h / 760 Torr / Ambient temperature

5: 1.) pyridine, 2.) Ac₂O / 1.) 90 deg C, 1 h, 2.) 90 deg C, 2 h

6: 87 percent / BF₃*Et₂O / 0.08 h / Ambient temperature

7: 85 percent / TMSOTf / acetonitrile / 8 h / -20 °C

8: 1.) O₃, 2.) Me₂S / 1.) MeOH, CH₂Cl₂, -78 deg C, 15 min

9: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 20 min, 2.) THF, 5 min

10: 79 percent / camphorsulfonic acid, triethyl orthoformate / benzene / 168 h / Ambient temperature

11: DBU / methanol / 5 h / Ambient temperature

12: Dess-Martin periodinane, 4 Angstroem molecular sieves / CH₂Cl₂ / 10 h / Ambient temperature

13: (Ph₃P)3RhCl / xylene / 0.75 h / Heating

With pyridine; 1H-imidazole; Wilkinson's catalyst; n-butyllithium; sodium azide; dimethylsulfide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; hydrogen; acetic anhydride; tetra-(n-butyl)ammonium iodide; sodium hydride; Dess-Martin periodane; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; orthoformic acid triethyl ester; Lindlar's catalyst; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; 2-methoxy-ethanol; water; acetonitrile; xylene; benzene;
DOI:10.1021/jo00112a040

Reference yield:

: (1S,2S,3S,4R,5R)-4-Azido-2-(2-methyl-allyl)-6,8-dioxa-bicyclo[3.2.1]octan-3-ol

: 163041-05-2
2-[(2S,3S,4S,5R)-4-Benzyloxy-2-[(E)-10-(4-methoxy-benzyloxy)-dec-2-enyl]-5-(2-methyl-[1,3]dioxolan-2-ylmethyl)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

Guidance literature:: Multi-step reaction with 11 steps

1: 1.) NaH, imidazole, 2.) n-tetrabutylammonium iodide / 1.) THF, DMF, 0 deg C, 2.) r.t., 4 h

2: H₂ / Lindlar catalyst / ethanol / 24 h / 760 Torr / Ambient temperature

3: 1.) pyridine, 2.) Ac₂O / 1.) 90 deg C, 1 h, 2.) 90 deg C, 2 h

4: 87 percent / BF₃*Et₂O / 0.08 h / Ambient temperature

5: 85 percent / TMSOTf / acetonitrile / 8 h / -20 °C

6: 1.) O₃, 2.) Me₂S / 1.) MeOH, CH₂Cl₂, -78 deg C, 15 min

7: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 20 min, 2.) THF, 5 min

8: 79 percent / camphorsulfonic acid, triethyl orthoformate / benzene / 168 h / Ambient temperature

9: DBU / methanol / 5 h / Ambient temperature

10: Dess-Martin periodinane, 4 Angstroem molecular sieves / CH₂Cl₂ / 10 h / Ambient temperature

11: (Ph₃P)3RhCl / xylene / 0.75 h / Heating

With pyridine; 1H-imidazole; Wilkinson's catalyst; n-butyllithium; dimethylsulfide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; hydrogen; acetic anhydride; tetra-(n-butyl)ammonium iodide; sodium hydride; Dess-Martin periodane; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; orthoformic acid triethyl ester; Lindlar's catalyst; In methanol; ethanol; dichloromethane; acetonitrile; xylene; benzene;
DOI:10.1021/jo00112a040