(1S,2S,6R,8S)-2,9,9-trimethyl-4-[(1S)-1-phenylethyl]-3,5-dioxa-4-boratricyclo[6.1.1.02,6]decane

Base Information

Chemical Name:(1S,2S,6R,8S)-2,9,9-trimethyl-4-[(1S)-1-phenylethyl]-3,5-dioxa-4-boratricyclo[6.1.1.02,6]decane
CAS No.:76110-80-0
Molecular Formula:C₁₈H₂₅BO₂
Molecular Weight:284.206
Hs Code.:
DSSTox Substance ID:DTXSID901113734

Synonyms:76110-80-0;DTXSID901113734;(3aS,4S,6S,7aR)-3a,5,5-Trimethyl-2-((S)-1-phenylethyl)hexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole;(3aS,4S,6S,7aR)-Hexahydro-3a,5,5-trimethyl-2-[(1S)-1-phenylethyl]-4,6-methano-1,3,2-benzodioxaborole

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1S,2S,6R,8S)-2,9,9-trimethyl-4-[(1S)-1-phenylethyl]-3,5-dioxa-4-boratricyclo[6.1.1.02,6]decane

Chemical Property:

Hydrogen Bond Donor Count:0
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:284.1947602
Heavy Atom Count:21
Complexity:417

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Canonical SMILES:B1(OC2CC3CC(C3(C)C)C2(O1)C)C(C)C4=CC=CC=C4
Isomeric SMILES:B1(O[C@@H]2C[C@@H]3C[C@H]([C@@]2(O1)C)C3(C)C)[C@@H](C)C4=CC=CC=C4

Technology Process of (1S,2S,6R,8S)-2,9,9-trimethyl-4-[(1S)-1-phenylethyl]-3,5-dioxa-4-boratricyclo[6.1.1.02,6]decane

There total 3 articles about (1S,2S,6R,8S)-2,9,9-trimethyl-4-[(1S)-1-phenylethyl]-3,5-dioxa-4-boratricyclo[6.1.1.02,6]decane 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: 94.0%

: 2146-67-0
(dichloromethyl)lithium

: 76110-78-6
(3aS,4S,6S,7aR)-3a,5,5-trimethyl-2-phenylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole

: 76110-80-0
(+)-pinanediol (S)-1-phenylethane-1-boronate

Guidance literature:: With methylmagnesium bromide; In tetrahydrofuran; B- and Li-compound mixed at -100°C, kept at 0°C for 1 h, cooled to-78°C, treated with CH3MgBr, kept at 20°C overnight; worked up with aq. acid, extd. (ether), distd.; NMR, elem. anal.;
DOI:10.1021/ja00545a046

Reference yield: 69.0%

: 917-54-4
methyllithium

: 76110-79-7
(S)-(chloro(phenyl)methyl)boronic acid boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester

: 76110-80-0
(+)-pinanediol (S)-1-phenylethane-1-boronate

Guidance literature:: With lithium bromide; In tetrahydrofuran; boronate ester in THF was treated with equiv. amt. of MeLi and LiBr in ether at -78°C, a mixture was warmed to 20-25°C and stirred fpr 10-20 h; CH2Cl2 was added, filtration, distn.; elem. anal.;

Reference yield:

: 76110-79-7
(S)-(chloro(phenyl)methyl)boronic acid boronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester

: 76110-80-0
(+)-pinanediol (S)-1-phenylethane-1-boronate

Guidance literature:: With methylmagnesium bromide; In tetrahydrofuran; byproducts: MgBr2; boronate ester in THF was treated with equiv. amt. of MeMgBr in ether at -78°C, a mixture was warmed to 20-25°C and stirred fpr 10-20 h, inert atm.; aq. HCl was added, extn. (ether), distn.; elem. anal.;