(3R,9R,10R)-10-tert-butyldimethylsilyloxy-3-tert-butyldiphenylsilyloxy-heptadec-1-ene-4,6-diyne-9-ol

Base Information

Chemical Name:(3R,9R,10R)-10-tert-butyldimethylsilyloxy-3-tert-butyldiphenylsilyloxy-heptadec-1-ene-4,6-diyne-9-ol
CAS No.:209479-94-7
Molecular Formula:C₃₉H₅₈O₃Si₂
Molecular Weight:631.059
Hs Code.:

Synonyms:(3R,9R,10R)-10-tert-butyldimethylsilyloxy-3-tert-butyldiphenylsilyloxy-heptadec-1-ene-4,6-diyne-9-ol

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Chemical Property of (3R,9R,10R)-10-tert-butyldimethylsilyloxy-3-tert-butyldiphenylsilyloxy-heptadec-1-ene-4,6-diyne-9-ol

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Technology Process of (3R,9R,10R)-10-tert-butyldimethylsilyloxy-3-tert-butyldiphenylsilyloxy-heptadec-1-ene-4,6-diyne-9-ol

There total 24 articles about (3R,9R,10R)-10-tert-butyldimethylsilyloxy-3-tert-butyldiphenylsilyloxy-heptadec-1-ene-4,6-diyne-9-ol 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: 75.0%

: 209479-93-6
(4R,5R)-1-bromo-5-tert-butyldimethylsilyl-1-dodadecyn-4-ol

: 209479-88-9
tert-butyl((S)-1-penten-4-yn-3-yloxy)diphenylsilane

: 209479-94-7
(3R,9R,10R)-10-tert-butyldimethylsilyloxy-3-tert-butyldiphenylsilyloxy-heptadec-1-ene-4,6-diyne-9-ol

Guidance literature:: With hydroxylamine hydrochloride; ethylamine; copper(l) chloride; In methanol; at 0 ℃;
DOI:10.1055/s-1998-1775

Reference yield: 75.0%

: 209479-93-6
(4R,5R)-1-bromo-5-tert-butyldimethylsilyl-1-dodadecyn-4-ol

: 224636-36-6
3(R)-(tert-butyldiphenylsilyloxy)-1-penten-4-yne

: 209479-94-7
(3R,9R,10R)-10-tert-butyldimethylsilyloxy-3-tert-butyldiphenylsilyloxy-heptadec-1-ene-4,6-diyne-9-ol

Guidance literature:: With hydroxylamine hydrochloride; ethylamine; copper(l) chloride; In methanol; at 0 ℃; for 0.166667h;
DOI:10.1016/S0040-4020(99)00352-X

Reference yield:

: 4762-26-9
hexyltriphenylphosphonium bromide

: 209479-94-7
(3R,9R,10R)-10-tert-butyldimethylsilyloxy-3-tert-butyldiphenylsilyloxy-heptadec-1-ene-4,6-diyne-9-ol

Guidance literature:: Multi-step reaction with 11 steps

1: 87 percent / n-BuLi / hexane; tetrahydrofuran / -78 deg C to rt

2: 97 percent / H₂ / Pd/C / aq. ethanol / 6 h / Ambient temperature

3: H₅IO₆ / ethyl acetate / 3 h / Ambient temperature

4: NaBH₄ / ethanol / 3 h / Ambient temperature

5: pyridine / 0 deg C, 1 h, rt, 6 h

6: p-TsOH / methanol / Ambient temperature; overnight

7: K₂CO₃ / methanol / 2 h / Ambient temperature

8: 92 percent / AgNO₃, Py / tetrahydrofuran / 24 h / Ambient temperature

9: 93 percent / n-BuLi, BF₃*Et₂O / hexane; tetrahydrofuran / 1 h / -78 °C

10: 87 percent / NBS, AgNO₃ / acetone / 3 h / Ambient temperature

11: 75 percent / CuCl, NH₂OH*HCl, aq. EtNH₂ / methanol / 0.17 h / 0 °C

With pyridine; sodium tetrahydroborate; N-Bromosuccinimide; n-butyllithium; boron trifluoride diethyl etherate; hydroxylamine hydrochloride; hydrogen; potassium carbonate; toluene-4-sulfonic acid; silver nitrate; ethylamine; periodic acid; copper(l) chloride; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; ethanol; hexane; ethyl acetate; acetone;
DOI:10.1016/S0040-4020(99)00352-X