3-[(2R)-2-[bis(trimethylsilyl)amino]-2-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl]-2-methoxy-benzoic acid 1,1-dimethylethyl ester

Base Information

Chemical Name:3-[(2R)-2-[bis(trimethylsilyl)amino]-2-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl]-2-methoxy-benzoic acid 1,1-dimethylethyl ester
CAS No.:1256336-53-4
Molecular Formula:C₃₀H₅₂BNO₅Si₂
Molecular Weight:573.729
Hs Code.:

3-[(2R)-2-[bis(trimethylsilyl)amino]-2-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl]-2-methoxy-benzoic acid 1,1-dimethylethyl ester

Synonyms:3-[(2R)-2-[bis(trimethylsilyl)amino]-2-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl]-2-methoxy-benzoic acid 1,1-dimethylethyl ester

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Chemical Property of 3-[(2R)-2-[bis(trimethylsilyl)amino]-2-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl]-2-methoxy-benzoic acid 1,1-dimethylethyl ester

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Technology Process of 3-[(2R)-2-[bis(trimethylsilyl)amino]-2-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl]-2-methoxy-benzoic acid 1,1-dimethylethyl ester

There total 11 articles about 3-[(2R)-2-[bis(trimethylsilyl)amino]-2-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl]-2-methoxy-benzoic acid 1,1-dimethylethyl 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:

: 1613269-49-0
tert-butyl 3-((2S)-2-chloro-2-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)ethyl)-2-methoxybenzoate

: 4039-32-1
lithium hexamethyldisilazane

: 1256336-53-4
3-[(2R)-2-[bis(trimethylsilyl)amino]-2-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl]-2-methoxy-benzoic acid 1,1-dimethylethyl ester

Guidance literature:: In tetrahydrofuran; at -78 ℃; for 16.75h; Temperature; Time;

Reference yield:

: 75-09-2
dichloromethane

: 1155425-68-5
2-methoxy-3-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]dec-4-ylmethyl)-benzoic acid tert-butyl ester

: 4039-32-1
lithium hexamethyldisilazane

: 1256336-53-4
3-[(2R)-2-[bis(trimethylsilyl)amino]-2-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl]-2-methoxy-benzoic acid 1,1-dimethylethyl ester

Guidance literature:: dichloromethane; With n-butyllithium; In tetrahydrofuran; hexane; at -100 ℃; for 0.5h; Inert atmosphere;

2-methoxy-3-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]dec-4-ylmethyl)-benzoic acid tert-butyl ester; In tetrahydrofuran; hexane; at -100 - 0 ℃; Inert atmosphere;

lithium hexamethyldisilazane; In tetrahydrofuran; hexane; at -78 - 20 ℃; Product distribution / selectivity; Inert atmosphere;

Reference yield:

: 913836-10-9
3-(dihydroxyboranyl)-2-methoxybenzoic acid

: 1256336-53-4
3-[(2R)-2-[bis(trimethylsilyl)amino]-2-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl]-2-methoxy-benzoic acid 1,1-dimethylethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: toluene / 3 h

2.1: thionyl chloride / 1 h / 95 °C

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.42 h / -5 °C

3.2: 4 h

4.1: n-butyllithium / tetrahydrofuran; hexane / 1.58 h / Cooling

4.2: 16.5 h

5.1: tetrahydrofuran / 0.5 h / -60 °C

5.2: 0.5 h / -60 °C

5.3: 1.5 h / -16 - 0 °C

6.1: tetrahydrofuran / 16.75 h / -78 °C

With n-butyllithium; thionyl chloride; In tetrahydrofuran; hexane; toluene;