5(R)-[4-bromo-2(R)-(tert-butyldiphenylsilanyloxy)but-3(Z)-enyl]-2,2,4(S)-trimethyl-[1,3]dioxolane-4(S)-carbaldehyde

Base Information

• Chemical Name: 5(R)-[4-bromo-2(R)-(tert-butyldiphenylsilanyloxy)but-3(Z)-enyl]-2,2,4(S)-trimethyl-[1,3]dioxolane-4(S)-carbaldehyde
• CAS No.: 411242-03-0
• Molecular Formula: C₂₇H₃₅BrO₄Si
• Molecular Weight: 531.562

Synonyms:5(R)-[4-bromo-2(R)-(tert-butyldiphenylsilanyloxy)but-3(Z)-enyl]-2,2,4(S)-trimethyl-[1,3]dioxolane-4(S)-carbaldehyde

Chemical Property of 5(R)-[4-bromo-2(R)-(tert-butyldiphenylsilanyloxy)but-3(Z)-enyl]-2,2,4(S)-trimethyl-[1,3]dioxolane-4(S)-carbaldehyde

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Technology Process of 5(R)-[4-bromo-2(R)-(tert-butyldiphenylsilanyloxy)but-3(Z)-enyl]-2,2,4(S)-trimethyl-[1,3]dioxolane-4(S)-carbaldehyde

There total 9 articles about 5(R)-[4-bromo-2(R)-(tert-butyldiphenylsilanyloxy)but-3(Z)-enyl]-2,2,4(S)-trimethyl-[1,3]dioxolane-4(S)-carbaldehyde 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%

{5(R)-[4-bromo-2(R)-(tert-butyldiphenylsilanyloxy)but-3(Z)-enyl]-2,2,4(R)-trimethyl-[1,3]dioxolane-4(R)-yl}methanol (411242-02-9) → 5(R)-[4-bromo-2(R)-(tert-butyldiphenylsilanyloxy)but-3(Z)-enyl]-2,2,4(S)-trimethyl-[1,3]dioxolane-4(S)-carbaldehyde (411242-03-0)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; at -78 - 0 ℃; for 2h;

DOI:10.1021/ol025537r

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → 5(R)-[4-bromo-2(R)-(tert-butyldiphenylsilanyloxy)but-3(Z)-enyl]-2,2,4(S)-trimethyl-[1,3]dioxolane-4(S)-carbaldehyde (411242-03-0)

Guidance literature:

Multi-step reaction with 8 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

With 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; In tetrahydrofuran; dichloromethane; water; acetone; tert-butyl alcohol; benzene; 4.1: Sharpless asymmetric dihydroxylation / 8.1: Swern oxidation;

DOI:10.1021/ol025537r

Reference yield:

5-hexen-1-yn-3(R)-ol (208336-98-5) → 5(R)-[4-bromo-2(R)-(tert-butyldiphenylsilanyloxy)but-3(Z)-enyl]-2,2,4(S)-trimethyl-[1,3]dioxolane-4(S)-carbaldehyde (411242-03-0)

Guidance literature:

Multi-step reaction with 8 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

With 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; In tetrahydrofuran; dichloromethane; water; acetone; tert-butyl alcohol; benzene; 4.1: Sharpless asymmetric dihydroxylation / 8.1: Swern oxidation;

DOI:10.1021/ol025537r

upstream raw materials:

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

tert-butylchlorodiphenylsilane

5-hexen-1-yn-3(R)-ol

3(R)-(tert-butyldiphenylsilanyloxy)pent-4-ynal

Downstream raw materials:

1-[1(R)-(tert-butyldimethylsilanyloxy)-1(R)-methyl-3-(6-oxo-3,6-dihydro-2H-pyran-2(R)-yl)allyl]-3(R),10-bis(tert-butyldiphenylsilanyloxy)-deca-4(Z),6(Z),8(E)-trienyl bis[2-(trimethylsilanyl)ethyl] phosphate

6(R)-[3(R)-(tert-butyldimethylsilanyloxy)-6(R),13-bis-(tert-butyldiphenylsilanyloxy)-4(R)-hydroxy-3(R)-methyltrideca-1(E),7(Z),9(Z),11(E)-tetraenyl]-5,6-dihydro-pyran-2-one

6(R)-[6(R),13-bis(tert-butyldiphenylsilanyloxy)-3(R),4(R)-dihydroxy-3(R)-methyltrideca-1(E),7(Z),9(Z),11(E)-tetraenyl]-5,6-dihydropyran-2-one

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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