1(R)-(2-{5(R)-[4-bromo-2(R)-(tert-butyldiphenylsilanyloxy)but-3(Z)-enyl]-2,2,4(R)-trimethyl-[1,3]dioxolan-4(R)-yl}vinyl)but-3-enyl acrylate

Base Information

Chemical Name:1(R)-(2-{5(R)-[4-bromo-2(R)-(tert-butyldiphenylsilanyloxy)but-3(Z)-enyl]-2,2,4(R)-trimethyl-[1,3]dioxolan-4(R)-yl}vinyl)but-3-enyl acrylate
CAS No.:411242-05-2
Molecular Formula:C₃₅H₄₅BrO₅Si
Molecular Weight:653.729
Hs Code.:

Synonyms:1(R)-(2-{5(R)-[4-bromo-2(R)-(tert-butyldiphenylsilanyloxy)but-3(Z)-enyl]-2,2,4(R)-trimethyl-[1,3]dioxolan-4(R)-yl}vinyl)but-3-enyl acrylate

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Chemical Property of 1(R)-(2-{5(R)-[4-bromo-2(R)-(tert-butyldiphenylsilanyloxy)but-3(Z)-enyl]-2,2,4(R)-trimethyl-[1,3]dioxolan-4(R)-yl}vinyl)but-3-enyl acrylate

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Technology Process of 1(R)-(2-{5(R)-[4-bromo-2(R)-(tert-butyldiphenylsilanyloxy)but-3(Z)-enyl]-2,2,4(R)-trimethyl-[1,3]dioxolan-4(R)-yl}vinyl)but-3-enyl acrylate

There total 12 articles about 1(R)-(2-{5(R)-[4-bromo-2(R)-(tert-butyldiphenylsilanyloxy)but-3(Z)-enyl]-2,2,4(R)-trimethyl-[1,3]dioxolan-4(R)-yl}vinyl)but-3-enyl acrylate 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: 86.0%

: 814-68-6,25189-84-8
acryloyl chloride

: 411242-15-4
1-{5(R)-[4-bromo-2(R)-(tert-butyldiphenylsilanyloxy)but-3(Z)-enyl]-2,2,4(R)-trimethyl-[1,3]dioxolan-4(R)-yl}hexa-1(E),5-dien-3(R)-ol

: 411242-05-2
1(R)-(2-{5(R)-[4-bromo-2(R)-(tert-butyldiphenylsilanyloxy)but-3(Z)-enyl]-2,2,4(R)-trimethyl-[1,3]dioxolan-4(R)-yl}vinyl)but-3-enyl acrylate

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 2h;
DOI:10.1021/ol025537r

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 411242-05-2
1(R)-(2-{5(R)-[4-bromo-2(R)-(tert-butyldiphenylsilanyloxy)but-3(Z)-enyl]-2,2,4(R)-trimethyl-[1,3]dioxolan-4(R)-yl}vinyl)but-3-enyl acrylate

Guidance literature:: Multi-step reaction with 11 steps

1.1: 88 percent / imidazole / CH₂Cl₂ / 4 h / 23 °C

2.1: OsO₄; N-methylmorpholine N-oxide / acetone; H₂O / 4 h / 20 °C

2.2: 64 percent / NaIO₄/SiO₂ / CH₂Cl₂ / 2 h / 23 °C

3.1: 87 percent / benzene / 12 h / 23 °C

4.1: AD-mix-β / 2-methyl-propan-2-ol; H2O / 48 h / 4 °C

4.2: 3.63 g / PPTS / CH₂Cl₂ / 8 h / 23 °C

5.1: 82 percent / N-bromosuccinimide; AgNO₃ / acetone / 2 h / 23 °C

6.1: 85 percent / (KO₂CN=)2; AcOH / tetrahydrofuran / 24 h / 23 °C

7.1: 83 percent / LiAlH₄ / tetrahydrofuran / 3 h / 0 - 23 °C

8.1: 86 percent / (ClCO)2; DMSO; Et₃N / 2 h / -78 - 0 °C

9.1: 88 percent / CH₂Cl₂ / 8 h / 40 °C

10.1: (+)-B-methoxydiisopinocampheylborane / diethyl ether / 1.5 h / -78 - 23 °C

10.2: H₂O₂ / diethyl ether / 1 h / -100 °C

10.3: 82 percent / aq.H₂O₂ / diethyl ether; ethanol; tetrahydrofuran / 12 h / 20 °C / pH 7

11.1: 86 percent / DIPEA / CH₂Cl₂ / 2 h / 0 °C

With (+)-Ipc₂BOMe; 1H-imidazole; N-Bromosuccinimide; osmium(VIII) oxide; lithium aluminium tetrahydride; oxalyl dichloride; AD-mix-β; potassium diazodicarboxylate; silver nitrate; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetone; tert-butyl alcohol; benzene; 4.1: Sharpless asymmetric dihydroxylation / 8.1: Swern oxidation;
DOI:10.1021/ol025537r

Reference yield:

: 208336-98-5
5-hexen-1-yn-3(R)-ol

: 411242-05-2
1(R)-(2-{5(R)-[4-bromo-2(R)-(tert-butyldiphenylsilanyloxy)but-3(Z)-enyl]-2,2,4(R)-trimethyl-[1,3]dioxolan-4(R)-yl}vinyl)but-3-enyl acrylate

Guidance literature:: Multi-step reaction with 11 steps

1.1: 88 percent / imidazole / CH₂Cl₂ / 4 h / 23 °C

2.1: OsO₄; N-methylmorpholine N-oxide / acetone; H₂O / 4 h / 20 °C

2.2: 64 percent / NaIO₄/SiO₂ / CH₂Cl₂ / 2 h / 23 °C

3.1: 87 percent / benzene / 12 h / 23 °C

4.1: AD-mix-β / 2-methyl-propan-2-ol; H2O / 48 h / 4 °C

4.2: 3.63 g / PPTS / CH₂Cl₂ / 8 h / 23 °C

5.1: 82 percent / N-bromosuccinimide; AgNO₃ / acetone / 2 h / 23 °C

6.1: 85 percent / (KO₂CN=)2; AcOH / tetrahydrofuran / 24 h / 23 °C

7.1: 83 percent / LiAlH₄ / tetrahydrofuran / 3 h / 0 - 23 °C

8.1: 86 percent / (ClCO)2; DMSO; Et₃N / 2 h / -78 - 0 °C

9.1: 88 percent / CH₂Cl₂ / 8 h / 40 °C

10.1: (+)-B-methoxydiisopinocampheylborane / diethyl ether / 1.5 h / -78 - 23 °C

10.2: H₂O₂ / diethyl ether / 1 h / -100 °C

10.3: 82 percent / aq.H₂O₂ / diethyl ether; ethanol; tetrahydrofuran / 12 h / 20 °C / pH 7

11.1: 86 percent / DIPEA / CH₂Cl₂ / 2 h / 0 °C

With (+)-Ipc₂BOMe; 1H-imidazole; N-Bromosuccinimide; osmium(VIII) oxide; lithium aluminium tetrahydride; oxalyl dichloride; AD-mix-β; potassium diazodicarboxylate; silver nitrate; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetone; tert-butyl alcohol; benzene; 4.1: Sharpless asymmetric dihydroxylation / 8.1: Swern oxidation;
DOI:10.1021/ol025537r