(4R,5S)-4-((R)-1-Benzyloxy-propyl)-2,2-dimethyl-5-trityloxymethyl-4-vinyl-[1,3]dioxolane

Base Information

Chemical Name:(4R,5S)-4-((R)-1-Benzyloxy-propyl)-2,2-dimethyl-5-trityloxymethyl-4-vinyl-[1,3]dioxolane
CAS No.:1054611-03-8
Molecular Formula:C₃₇H₄₀O₄
Molecular Weight:548.722
Hs Code.:

Synonyms:(4R,5S)-4-((R)-1-Benzyloxy-propyl)-2,2-dimethyl-5-trityloxymethyl-4-vinyl-[1,3]dioxolane

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Chemical Property of (4R,5S)-4-((R)-1-Benzyloxy-propyl)-2,2-dimethyl-5-trityloxymethyl-4-vinyl-[1,3]dioxolane

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Technology Process of (4R,5S)-4-((R)-1-Benzyloxy-propyl)-2,2-dimethyl-5-trityloxymethyl-4-vinyl-[1,3]dioxolane

There total 9 articles about (4R,5S)-4-((R)-1-Benzyloxy-propyl)-2,2-dimethyl-5-trityloxymethyl-4-vinyl-[1,3]dioxolane 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:

: 100-39-0
benzyl bromide

: (R)-1-((4R,5S)-2,2-Dimethyl-5-trityloxymethyl-4-vinyl-[1,3]dioxolan-4-yl)-propan-1-ol

: 1054611-03-8
(4R,5S)-4-((R)-1-Benzyloxy-propyl)-2,2-dimethyl-5-trityloxymethyl-4-vinyl-[1,3]dioxolane

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide;

Reference yield:

: 16749-42-1
5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose

: 1054611-03-8
(4R,5S)-4-((R)-1-Benzyloxy-propyl)-2,2-dimethyl-5-trityloxymethyl-4-vinyl-[1,3]dioxolane

Guidance literature:: Multi-step reaction with 8 steps

1: pyridinium chlorochromate; molecular sieves 4 Angstroem / CH₂Cl₂ / 10 h / 20 °C

2: tetrahydrofuran / 1 h / -18 °C

3: aq. AcOH / 11 h / 80 °C

4: 5.60 g / N-iodosuccinimide; n-Bu₄NI / CH₂Cl₂ / 20 h / 20 °C

5: 79 percent / CSA / acetone / 6 h / 40 °C / 225.02 Torr

6: 91 percent / LiAlH₄ / tetrahydrofuran / 2 h / 0 °C

7: DMAP; pyridine / 4 h / Heating

8: NaH / dimethylformamide / 8 h / 20 °C

With pyridine; dmap; N-iodo-succinimide; lithium aluminium tetrahydride; 4 A molecular sieve; camphor-10-sulfonic acid; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1246/bcsj.77.1703

Reference yield:

: 499120-93-3
(2R,3R,4R,5R)-5-ethyl-4-hydroxy-2,3-isopropylidenedioxy-4-vinyltetrahydrofuran

: 1054611-03-8
(4R,5S)-4-((R)-1-Benzyloxy-propyl)-2,2-dimethyl-5-trityloxymethyl-4-vinyl-[1,3]dioxolane

Guidance literature:: Multi-step reaction with 6 steps

1: aq. AcOH / 11 h / 80 °C

2: 5.60 g / N-iodosuccinimide; n-Bu₄NI / CH₂Cl₂ / 20 h / 20 °C

3: 79 percent / CSA / acetone / 6 h / 40 °C / 225.02 Torr

4: 91 percent / LiAlH₄ / tetrahydrofuran / 2 h / 0 °C

5: DMAP; pyridine / 4 h / Heating

6: NaH / dimethylformamide / 8 h / 20 °C

With pyridine; dmap; N-iodo-succinimide; lithium aluminium tetrahydride; camphor-10-sulfonic acid; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1246/bcsj.77.1703