(4R,7R)-7-(benzyloxy)-7-((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)hept-1-en-4-ol

Base Information

Chemical Name:(4R,7R)-7-(benzyloxy)-7-((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)hept-1-en-4-ol
CAS No.:386761-60-0
Molecular Formula:C₁₉H₂₈O₄
Molecular Weight:320.429
Hs Code.:

Synonyms:(4R,7R)-7-(benzyloxy)-7-((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)hept-1-en-4-ol

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Chemical Property of (4R,7R)-7-(benzyloxy)-7-((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)hept-1-en-4-ol

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Technology Process of (4R,7R)-7-(benzyloxy)-7-((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)hept-1-en-4-ol

There total 7 articles about (4R,7R)-7-(benzyloxy)-7-((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)hept-1-en-4-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: 81.0%

: 2622-05-1
allylmagnesium bromide

: 386761-70-2
(4R)-4-(benzyloxy)-4-((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)butanal

: 386761-60-0
(4R,7R)-7-(benzyloxy)-7-((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)hept-1-en-4-ol

Guidance literature:: allylmagnesium bromide; chiral titanium complex; In diethyl ether; at 0 ℃; for 2h;

(4R)-4-(benzyloxy)-4-((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)butanal; In diethyl ether; at -78 ℃; for 3h; Further stages.;
DOI:10.1021/jo010653d

Reference yield:

: 87604-46-4
(2R,3R)-1,2-O-isopropylidene-5-hexene-1,2,3-triol

: 386761-60-0
(4R,7R)-7-(benzyloxy)-7-((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)hept-1-en-4-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 91 percent / t-BuOK / tetrahydrofuran / 2.5 h / 20 °C

2.1: BH₃ / tetrahydrofuran / 2 h / 20 °C

2.2: 83 percent / aq. H₂O₂; aq. NaOH / tetrahydrofuran; H₂O / 2.3 h / 20 °C

3.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

4.1: chiral titanium complex / diethyl ether / 2 h / 0 °C

4.2: 81 percent / diethyl ether / 3 h / -78 °C

With oxalyl dichloride; borane; potassium tert-butylate; dimethyl sulfoxide; triethylamine; chiral titanium complex; In tetrahydrofuran; diethyl ether; dichloromethane; 3.1: Swern oxidation;
DOI:10.1021/jo010653d

Reference yield:

: 87604-54-4
(R)-4-((R)-1-(benzyloxy)but-3-en-1-yl)-2,2-dimethyl-1,3-dioxolane

: 386761-60-0
(4R,7R)-7-(benzyloxy)-7-((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)hept-1-en-4-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: BH₃ / tetrahydrofuran / 2 h / 20 °C

1.2: 83 percent / aq. H₂O₂; aq. NaOH / tetrahydrofuran; H₂O / 2.3 h / 20 °C

2.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

3.1: chiral titanium complex / diethyl ether / 2 h / 0 °C

3.2: 81 percent / diethyl ether / 3 h / -78 °C

With oxalyl dichloride; borane; dimethyl sulfoxide; triethylamine; chiral titanium complex; In tetrahydrofuran; diethyl ether; dichloromethane; 2.1: Swern oxidation;
DOI:10.1021/jo010653d