(4R,5S)-4-[3-((4S,5R)-5-{(2S,3S)-3-[(tert-butyldiphenylsilyl)oxy]-2-hydroxypentyl}-2,2-dimethyl-1,3-dioxolan-4-yl)prop-1-yn-1-yl]-5-[(4-methoxyphenoxy)methyl]-1,3-dioxolan-2-one

Base Information

Chemical Name:(4R,5S)-4-[3-((4S,5R)-5-{(2S,3S)-3-[(tert-butyldiphenylsilyl)oxy]-2-hydroxypentyl}-2,2-dimethyl-1,3-dioxolan-4-yl)prop-1-yn-1-yl]-5-[(4-methoxyphenoxy)methyl]-1,3-dioxolan-2-one
CAS No.:1439510-82-3
Molecular Formula:C₄₀H₅₀O₉Si
Molecular Weight:702.917
Hs Code.:

(4R,5S)-4-[3-((4S,5R)-5-{(2S,3S)-3-[(tert-butyldiphenylsilyl)oxy]-2-hydroxypentyl}-2,2-dimethyl-1,3-dioxolan-4-yl)prop-1-yn-1-yl]-5-[(4-methoxyphenoxy)methyl]-1,3-dioxolan-2-one

Synonyms:(4R,5S)-4-[3-((4S,5R)-5-{(2S,3S)-3-[(tert-butyldiphenylsilyl)oxy]-2-hydroxypentyl}-2,2-dimethyl-1,3-dioxolan-4-yl)prop-1-yn-1-yl]-5-[(4-methoxyphenoxy)methyl]-1,3-dioxolan-2-one

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Chemical Property of (4R,5S)-4-[3-((4S,5R)-5-{(2S,3S)-3-[(tert-butyldiphenylsilyl)oxy]-2-hydroxypentyl}-2,2-dimethyl-1,3-dioxolan-4-yl)prop-1-yn-1-yl]-5-[(4-methoxyphenoxy)methyl]-1,3-dioxolan-2-one

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Technology Process of (4R,5S)-4-[3-((4S,5R)-5-{(2S,3S)-3-[(tert-butyldiphenylsilyl)oxy]-2-hydroxypentyl}-2,2-dimethyl-1,3-dioxolan-4-yl)prop-1-yn-1-yl]-5-[(4-methoxyphenoxy)methyl]-1,3-dioxolan-2-one

There total 15 articles about (4R,5S)-4-[3-((4S,5R)-5-{(2S,3S)-3-[(tert-butyldiphenylsilyl)oxy]-2-hydroxypentyl}-2,2-dimethyl-1,3-dioxolan-4-yl)prop-1-yn-1-yl]-5-[(4-methoxyphenoxy)methyl]-1,3-dioxolan-2-one 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:

: C₄₇H₅₄O₁₁SSi

: 1439510-82-3
(4R,5S)-4-[3-((4S,5R)-5-{(2S,3S)-3-[(tert-butyldiphenylsilyl)oxy]-2-hydroxypentyl}-2,2-dimethyl-1,3-dioxolan-4-yl)prop-1-yn-1-yl]-5-[(4-methoxyphenoxy)methyl]-1,3-dioxolan-2-one

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; at 80 ℃; for 0.666667h; Inert atmosphere;
DOI:10.1021/ol401231y

Reference yield:

: 1439510-39-0
{(4S,5R)-2,2-dimethyl-5-[(E)-pent-2-en-1-yl]-1,3-dioxolan-4-yl}methanol

: 1439510-82-3
(4R,5S)-4-[3-((4S,5R)-5-{(2S,3S)-3-[(tert-butyldiphenylsilyl)oxy]-2-hydroxypentyl}-2,2-dimethyl-1,3-dioxolan-4-yl)prop-1-yn-1-yl]-5-[(4-methoxyphenoxy)methyl]-1,3-dioxolan-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 0.25 h / 20 °C / Inert atmosphere

2: chromium dichloride; nickel dichloride / tetrahydrofuran / 1.17 h / 0 - 20 °C / Inert atmosphere

3: dmap / acetonitrile / 0.17 h / 0 °C / Inert atmosphere

4: sodium hydrogencarbonate; osmium(VIII) oxide; potassium hexacyanoperferrate; methanesulfonamide; potassium carbonate; hydroquinidein 1,4-phthalazinediyl diether / water; tert-butyl alcohol / 1.5 h / 0 °C

5: 2,6-dimethylpyridine / dichloromethane / 3 h / -78 °C / Inert atmosphere

6: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / benzene / 0.67 h / 80 °C / Inert atmosphere

With 2,6-dimethylpyridine; chromium dichloride; dmap; osmium(VIII) oxide; potassium hexacyanoperferrate; 2,2'-azobis(isobutyronitrile); methanesulfonamide; tri-n-butyl-tin hydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; hydroquinidein 1,4-phthalazinediyl diether; nickel dichloride; In tetrahydrofuran; dichloromethane; water; acetonitrile; tert-butyl alcohol; benzene; 1: |Dess-Martin Oxidation / 2: |Nozaki-Hiyama-Kishi Reaction / 4: |Sharpless Dihydroxylation / 6: |Barton-McCombie Deoxygenation;
DOI:10.1021/ol401231y

Reference yield:

: 1439510-53-8
(4R,5S)-4-ethynyl-5-[(4-methoxyphenoxy)methyl]-2,2-dimethyl-1,3-dioxolane

: 1439510-82-3
(4R,5S)-4-[3-((4S,5R)-5-{(2S,3S)-3-[(tert-butyldiphenylsilyl)oxy]-2-hydroxypentyl}-2,2-dimethyl-1,3-dioxolan-4-yl)prop-1-yn-1-yl]-5-[(4-methoxyphenoxy)methyl]-1,3-dioxolan-2-one

Guidance literature:: Multi-step reaction with 8 steps

1: toluene-4-sulfonic acid / methanol / 17 h / 20 °C / Inert atmosphere

2: pyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

3: N-iodo-succinimide; silver nitrate / acetone / 0.25 h / 20 °C / Inert atmosphere

4: chromium dichloride; nickel dichloride / tetrahydrofuran / 1.17 h / 0 - 20 °C / Inert atmosphere

5: dmap / acetonitrile / 0.17 h / 0 °C / Inert atmosphere

6: sodium hydrogencarbonate; osmium(VIII) oxide; potassium hexacyanoperferrate; methanesulfonamide; potassium carbonate; hydroquinidein 1,4-phthalazinediyl diether / water; tert-butyl alcohol / 1.5 h / 0 °C

7: 2,6-dimethylpyridine / dichloromethane / 3 h / -78 °C / Inert atmosphere

8: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / benzene / 0.67 h / 80 °C / Inert atmosphere

With pyridine; 2,6-dimethylpyridine; chromium dichloride; dmap; N-iodo-succinimide; osmium(VIII) oxide; potassium hexacyanoperferrate; 2,2'-azobis(isobutyronitrile); methanesulfonamide; tri-n-butyl-tin hydride; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; silver nitrate; hydroquinidein 1,4-phthalazinediyl diether; nickel dichloride; In tetrahydrofuran; methanol; dichloromethane; water; acetone; acetonitrile; tert-butyl alcohol; benzene; 4: |Nozaki-Hiyama-Kishi Reaction / 6: |Sharpless Dihydroxylation / 8: |Barton-McCombie Deoxygenation;
DOI:10.1021/ol401231y