(2E)-2-{(1R,4Z,8S)-8-hydroxy-10-[(methoxycarbonyl)amino]-1-[(triethylsilyl)oxy]-13H-spiro[bicyclo[7.3.1]trideca-4,9-diene-2,6-diyne-11,2'-[1,3]dioxolan]-13-ylidene}ethyl benzoate

Base Information

Chemical Name:(2E)-2-{(1R,4Z,8S)-8-hydroxy-10-[(methoxycarbonyl)amino]-1-[(triethylsilyl)oxy]-13H-spiro[bicyclo[7.3.1]trideca-4,9-diene-2,6-diyne-11,2'-[1,3]dioxolan]-13-ylidene}ethyl benzoate
CAS No.:144668-33-7
Molecular Formula:C₃₂H₃₇NO₈Si
Molecular Weight:591.733
Hs Code.:

(2E)-2-{(1R,4Z,8S)-8-hydroxy-10-[(methoxycarbonyl)amino]-1-[(triethylsilyl)oxy]-13H-spiro[bicyclo[7.3.1]trideca-4,9-diene-2,6-diyne-11,2'-[1,3]dioxolan]-13-ylidene}ethyl benzoate

Synonyms:(2E)-2-{(1R,4Z,8S)-8-hydroxy-10-[(methoxycarbonyl)amino]-1-[(triethylsilyl)oxy]-13H-spiro[bicyclo[7.3.1]trideca-4,9-diene-2,6-diyne-11,2'-[1,3]dioxolan]-13-ylidene}ethyl benzoate

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Chemical Property of (2E)-2-{(1R,4Z,8S)-8-hydroxy-10-[(methoxycarbonyl)amino]-1-[(triethylsilyl)oxy]-13H-spiro[bicyclo[7.3.1]trideca-4,9-diene-2,6-diyne-11,2'-[1,3]dioxolan]-13-ylidene}ethyl benzoate

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Technology Process of (2E)-2-{(1R,4Z,8S)-8-hydroxy-10-[(methoxycarbonyl)amino]-1-[(triethylsilyl)oxy]-13H-spiro[bicyclo[7.3.1]trideca-4,9-diene-2,6-diyne-11,2'-[1,3]dioxolan]-13-ylidene}ethyl benzoate

There total 20 articles about (2E)-2-{(1R,4Z,8S)-8-hydroxy-10-[(methoxycarbonyl)amino]-1-[(triethylsilyl)oxy]-13H-spiro[bicyclo[7.3.1]trideca-4,9-diene-2,6-diyne-11,2'-[1,3]dioxolan]-13-ylidene}ethyl benzoate 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: 84.0%

: 98-88-4
benzoyl chloride

: 139609-43-1
methyl {(1R,4Z,8S,13E)-8-hydroxy-13-(2-hydroxyethylidene)-1-[(triethylsilyl)oxy]spiro[bicyclo[7.3.1]trideca-4,9-diene-2,6-diyne-11,2'-[1,3]dioxolan]-10-yl}carbamate

: 144668-33-7
(2E)-2-{(1R,4Z,8S)-8-hydroxy-10-[(methoxycarbonyl)amino]-1-[(triethylsilyl)oxy]-13H-spiro[bicyclo[7.3.1]trideca-4,9-diene-2,6-diyne-11,2'-[1,3]dioxolan]-13-ylidene}ethyl benzoate

: C₃₉H₄₁NO₉Si

Guidance literature:: With pyridine; In dichloromethane; at -15 ℃;
DOI:10.1021/ja00070a006

Reference yield: 84.0%

: 98-88-4
benzoyl chloride

: 139609-43-1
methyl {(1R,4Z,8S,13E)-8-hydroxy-13-(2-hydroxyethylidene)-1-[(triethylsilyl)oxy]spiro[bicyclo[7.3.1]trideca-4,9-diene-2,6-diyne-11,2'-[1,3]dioxolan]-10-yl}carbamate

: 144668-33-7
(2E)-2-{(1R,4Z,8S)-8-hydroxy-10-[(methoxycarbonyl)amino]-1-[(triethylsilyl)oxy]-13H-spiro[bicyclo[7.3.1]trideca-4,9-diene-2,6-diyne-11,2'-[1,3]dioxolan]-13-ylidene}ethyl benzoate

Guidance literature:: With pyridine; In dichloromethane; at -15 ℃; for 1h; Inert atmosphere;
DOI:10.1021/jacs.8b06955

Reference yield:

: 139609-26-0,139684-83-6
(3aS,4R,5R)-5-(benzoyloxy)-3,3a,4,5,6,7-hexahydro-4-<(2-methoxyethoxy)methoxy>spiro<2,1-benzisoxazole-7,2'-<1,3>dioxolane>

: 144668-33-7
(2E)-2-{(1R,4Z,8S)-8-hydroxy-10-[(methoxycarbonyl)amino]-1-[(triethylsilyl)oxy]-13H-spiro[bicyclo[7.3.1]trideca-4,9-diene-2,6-diyne-11,2'-[1,3]dioxolan]-13-ylidene}ethyl benzoate

Guidance literature:: Multi-step reaction with 17 steps

1.1: sodium methylate / methanol / 12 h / 0 °C / Inert atmosphere

2.1: Jones reagent / acetone; water / 2 h / 0 °C / Inert atmosphere

3.1: lithium hexamethyldisilazane; lanthanium (III) chloride bis(lithium chloride) complex / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

3.2: 0.5 h / -78 °C / Inert atmosphere

4.1: tetrahydrofuran / 2 h / -78 - 25 °C / Inert atmosphere

5.1: chloro-trimethyl-silane; sodium iodide / acetonitrile / 0.5 h / 0 - 25 °C / Inert atmosphere

6.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

6.2: 1.5 h / -78 - 25 °C / Inert atmosphere

7.1: lithium hexamethyldisilazane / tetrahydrofuran / 1.5 h / -78 - 25 °C / Inert atmosphere

8.1: potassium carbonate / methanol; tetrahydrofuran / 3 h / 0 - 25 °C / Inert atmosphere

9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C / Inert atmosphere

10.1: 2,6-dimethylpyridine / dichloromethane / 2 h / 0 - 25 °C / Inert atmosphere

11.1: iron; ammonium chloride / water; ethanol / 8 h / 60 °C / Inert atmosphere

12.1: pyridine / nitromethane / 0.5 h / 0 °C / Inert atmosphere

12.2: 2 h / 25 °C / Inert atmosphere

12.3: 1 h / 25 °C / Inert atmosphere

13.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere

13.2: Inert atmosphere

14.1: methylhydrazine / benzene / 0.5 h / 25 °C / Inert atmosphere

15.1: pyridine / dichloromethane / 1 h / 0 °C / Inert atmosphere

15.2: 1 h / 0 °C / Inert atmosphere

16.1: cerium(III) chloride heptahydrate / methanol / 0.33 h / 25 °C / Inert atmosphere

16.2: 1 h / 25 °C / Inert atmosphere

17.1: pyridine / dichloromethane / 1 h / -15 °C / Inert atmosphere

With pyridine; 2,6-dimethylpyridine; Jones reagent; chloro-trimethyl-silane; oxalyl dichloride; lanthanium (III) chloride bis(lithium chloride) complex; cerium(III) chloride heptahydrate; tetrabutyl ammonium fluoride; sodium methylate; iron; potassium carbonate; ammonium chloride; dimethyl sulfoxide; methylhydrazine; sodium iodide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; nitromethane; ethanol; dichloromethane; water; acetone; acetonitrile; benzene; 16.1: |Luche Cerium Reduction / 16.2: |Luche Cerium Reduction;
DOI:10.1021/jacs.8b06955