(2R,8R,20R)-2-benzyloxy-22-(tert-butyldiphenylsilanyloxy)-20-(4-methoxybenzyloxy)docos-10-yn-8-ol

Base Information

Chemical Name:(2R,8R,20R)-2-benzyloxy-22-(tert-butyldiphenylsilanyloxy)-20-(4-methoxybenzyloxy)docos-10-yn-8-ol
CAS No.:725724-09-4
Molecular Formula:C₅₃H₇₄O₅Si
Molecular Weight:819.253
Hs Code.:

Synonyms:(2R,8R,20R)-2-benzyloxy-22-(tert-butyldiphenylsilanyloxy)-20-(4-methoxybenzyloxy)docos-10-yn-8-ol

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Chemical Property of (2R,8R,20R)-2-benzyloxy-22-(tert-butyldiphenylsilanyloxy)-20-(4-methoxybenzyloxy)docos-10-yn-8-ol

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Technology Process of (2R,8R,20R)-2-benzyloxy-22-(tert-butyldiphenylsilanyloxy)-20-(4-methoxybenzyloxy)docos-10-yn-8-ol

There total 14 articles about (2R,8R,20R)-2-benzyloxy-22-(tert-butyldiphenylsilanyloxy)-20-(4-methoxybenzyloxy)docos-10-yn-8-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: 91.0%

: 725723-98-8
(2R,6R)-2-(6-benzyloxyheptyl)oxirane

: 725723-97-7
(R)-tert-butyl[3-(4-methoxybenzyloxy)tridec-12-ynyloxy]diphenylsilane

: 725724-09-4
(2R,8R,20R)-2-benzyloxy-22-(tert-butyldiphenylsilanyloxy)-20-(4-methoxybenzyloxy)docos-10-yn-8-ol

Guidance literature:: (R)-tert-butyl[3-(4-methoxybenzyloxy)tridec-12-ynyloxy]diphenylsilane; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

(2R,6R)-2-(6-benzyloxyheptyl)oxirane; With boron trifluoride diethyl etherate; In tetrahydrofuran; hexane; at -78 ℃; for 1.5h;
DOI:10.1021/jo0496392

Reference yield:

: 116761-24-1
(R)-3-(benzyloxy)butanoic acid methyl ester

: 725724-09-4
(2R,8R,20R)-2-benzyloxy-22-(tert-butyldiphenylsilanyloxy)-20-(4-methoxybenzyloxy)docos-10-yn-8-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: 94 percent / LiAlH₄ / diethyl ether / 2 h / 0 °C

2.1: 77 percent / pyrdine / 3 h / 0 °C

3.1: magnesium / tetrahydrofuran

3.2: tetrahydrofuran / 0.5 h / 0 °C

3.3: 12.8 g / CuI / tetrahydrofuran / 15 h / 0 - 50 °C

4.1: 87 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 24 h / 0 - 20 °C

5.1: 44 percent / (R,R)-1,2-cyclohexanediamine based salen cobalt complex; acetic acid / toluene / 1 h / 20 °C

6.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

6.2: 91 percent / BF₃*Et₂O / tetrahydrofuran; hexane / 1.5 h / -78 °C

With pyridine; lithium aluminium tetrahydride; n-butyllithium; (R,R)-1,2-cyclohexanediamine based salen cobalt; magnesium; acetic acid; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene;
DOI:10.1021/jo0496392

Reference yield:

: 116757-62-1
(R)-3-O-benzyl-1,3-butanediol

: 725724-09-4
(2R,8R,20R)-2-benzyloxy-22-(tert-butyldiphenylsilanyloxy)-20-(4-methoxybenzyloxy)docos-10-yn-8-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 77 percent / pyrdine / 3 h / 0 °C

2.1: magnesium / tetrahydrofuran

2.2: tetrahydrofuran / 0.5 h / 0 °C

2.3: 12.8 g / CuI / tetrahydrofuran / 15 h / 0 - 50 °C

3.1: 87 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 24 h / 0 - 20 °C

4.1: 44 percent / (R,R)-1,2-cyclohexanediamine based salen cobalt complex; acetic acid / toluene / 1 h / 20 °C

5.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

5.2: 91 percent / BF₃*Et₂O / tetrahydrofuran; hexane / 1.5 h / -78 °C

With pyridine; n-butyllithium; (R,R)-1,2-cyclohexanediamine based salen cobalt; magnesium; acetic acid; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; hexane; dichloromethane; toluene;
DOI:10.1021/jo0496392