(4S,5S)-4-((2R,3R,5S,6R,8S)-8-{(S)-1-[(tert-butyldiphenylsilyl)oxy]propyl}-3,5,6-trihydroxyoxocan-2-yl)-5-[(4-methoxyphenoxy)methyl]-1,3-dioxolan-2-one

Base Information

• Chemical Name: (4S,5S)-4-((2R,3R,5S,6R,8S)-8-{(S)-1-[(tert-butyldiphenylsilyl)oxy]propyl}-3,5,6-trihydroxyoxocan-2-yl)-5-[(4-methoxyphenoxy)methyl]-1,3-dioxolan-2-one
• CAS No.: 1439511-04-2
• Molecular Formula: C₃₇H₄₈O₁₀Si
• Molecular Weight: 680.868

Synonyms:(4S,5S)-4-((2R,3R,5S,6R,8S)-8-{(S)-1-[(tert-butyldiphenylsilyl)oxy]propyl}-3,5,6-trihydroxyoxocan-2-yl)-5-[(4-methoxyphenoxy)methyl]-1,3-dioxolan-2-one

Chemical Property of (4S,5S)-4-((2R,3R,5S,6R,8S)-8-{(S)-1-[(tert-butyldiphenylsilyl)oxy]propyl}-3,5,6-trihydroxyoxocan-2-yl)-5-[(4-methoxyphenoxy)methyl]-1,3-dioxolan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (4S,5S)-4-((2R,3R,5S,6R,8S)-8-{(S)-1-[(tert-butyldiphenylsilyl)oxy]propyl}-3,5,6-trihydroxyoxocan-2-yl)-5-[(4-methoxyphenoxy)methyl]-1,3-dioxolan-2-one

There total 17 articles about (4S,5S)-4-((2R,3R,5S,6R,8S)-8-{(S)-1-[(tert-butyldiphenylsilyl)oxy]propyl}-3,5,6-trihydroxyoxocan-2-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: 49.0%

(4S,5S)-4-((2S,4R,5S,Z)-2-{(S)-1-[(tert-butyldiphenylsilyl)oxy]propyl}-4,5-dihydroxy-3,4,5,6-tetrahydro-2H-oxocin-8-yl)-5-[(4-methoxyphenoxy)methyl]-1,3-dioxolan-2-one → (4S,5S)-4-((2R,3R,5S,6R,8S)-8-{(S)-1-[(tert-butyldiphenylsilyl)oxy]propyl}-3,5,6-trihydroxyoxocan-2-yl)-5-[(4-methoxyphenoxy)methyl]-1,3-dioxolan-2-one (1439511-04-2)

Guidance literature:

(4S,5S)-4-((2S,4R,5S,Z)-2-{(S)-1-[(tert-butyldiphenylsilyl)oxy]propyl}-4,5-dihydroxy-3,4,5,6-tetrahydro-2H-oxocin-8-yl)-5-[(4-methoxyphenoxy)methyl]-1,3-dioxolan-2-one; With dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 20 ℃; for 2h; Inert atmosphere;

In tetrahydrofuran; water; at 0 - 20 ℃; for 1h; stereoselective reaction;

DOI:10.1021/ol401231y

Reference yield:

{(4S,5R)-2,2-dimethyl-5-[(E)-pent-2-en-1-yl]-1,3-dioxolan-4-yl}methanol (1439510-39-0) → (4S,5S)-4-((2R,3R,5S,6R,8S)-8-{(S)-1-[(tert-butyldiphenylsilyl)oxy]propyl}-3,5,6-trihydroxyoxocan-2-yl)-5-[(4-methoxyphenoxy)methyl]-1,3-dioxolan-2-one (1439511-04-2)

Guidance literature:

Multi-step reaction with 9 steps

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

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

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

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

5.1: 2,6-dimethylpyridine / dichloromethane / 3 h / -78 °C / Inert atmosphere

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

7.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 1,1'-bis-(diphenylphosphino)ferrocene; water / N,N-dimethyl-formamide / 0.58 h / 20 - 50 °C / Inert atmosphere

8.1: acetic acid / water; tetrahydrofuran / 4 h / 80 °C

9.1: dimethylsulfide borane complex / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

9.2: NaBO₃ / 1 h / 0 - 20 °C

With 2,6-dimethylpyridine; chromium dichloride; dmap; 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; osmium(VIII) oxide; potassium hexacyanoperferrate; 2,2'-azobis(isobutyronitrile); methanesulfonamide; dimethylsulfide borane complex; water; tri-n-butyl-tin hydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; acetic acid; hydroquinidein 1,4-phthalazinediyl diether; nickel dichloride; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; benzene; 1.1: |Dess-Martin Oxidation / 2.1: |Nozaki-Hiyama-Kishi Reaction / 4.1: |Sharpless Dihydroxylation / 6.1: |Barton-McCombie Deoxygenation;

DOI:10.1021/ol401231y

Reference yield:

[(4S,5R)-5-ethynyl-2,2-dimethyl-1,3-dioxolan-4-yl]methanol (127305-55-9) → (4S,5S)-4-((2R,3R,5S,6R,8S)-8-{(S)-1-[(tert-butyldiphenylsilyl)oxy]propyl}-3,5,6-trihydroxyoxocan-2-yl)-5-[(4-methoxyphenoxy)methyl]-1,3-dioxolan-2-one (1439511-04-2)

Guidance literature:

Multi-step reaction with 12 steps

1.1: triphenylphosphine; diethylazodicarboxylate / toluene / 1 h / 0 - 70 °C / Inert atmosphere

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

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

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

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

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

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

8.1: 2,6-dimethylpyridine / dichloromethane / 3 h / -78 °C / Inert atmosphere

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

10.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 1,1'-bis-(diphenylphosphino)ferrocene; water / N,N-dimethyl-formamide / 0.58 h / 20 - 50 °C / Inert atmosphere

11.1: acetic acid / water; tetrahydrofuran / 4 h / 80 °C

12.1: dimethylsulfide borane complex / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

12.2: NaBO₃ / 1 h / 0 - 20 °C

With pyridine; 2,6-dimethylpyridine; chromium dichloride; dmap; 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; N-iodo-succinimide; osmium(VIII) oxide; potassium hexacyanoperferrate; 2,2'-azobis(isobutyronitrile); methanesulfonamide; dimethylsulfide borane complex; water; tri-n-butyl-tin hydride; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; silver nitrate; acetic acid; hydroquinidein 1,4-phthalazinediyl diether; triphenylphosphine; nickel dichloride; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; tert-butyl alcohol; benzene; 1.1: |Mitsunobu Displacement / 5.1: |Nozaki-Hiyama-Kishi Reaction / 7.1: |Sharpless Dihydroxylation / 9.1: |Barton-McCombie Deoxygenation;

DOI:10.1021/ol401231y

upstream raw materials:

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

[(4S,5R)-5-ethynyl-2,2-dimethyl-1,3-dioxolan-4-yl]methanol

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

4-methoxy-phenol

Downstream raw materials:

(3aR,5S,6aS,7S,8S,9aS,10aS)-5-{(S)-1-[(tert-butyldiphenylsilyl)oxy]propyl}-8-[(4-methoxyphenoxy)methyl]-2,2-dimethyloctahydro-3aH-[1,3]dioxolo[4,5-e]furo[3,2-b]oxocin-7-ol

(3aR,5S,6aS,8R,9aS,10aS)-5-{(S)-1-[(tert-butyldiphenylsilyl)oxy]propyl-2,2-dimethyloctahydro-3aH-[1,3]dioxolo[4,5-e]furo[3,2-b]oxocin-8-yl}methanol

(S)-1-((3aR,5S,6aS,8R,9aS,10aS)-5-{(S)-1-hydroxypropyl}-2,2-dimethyloctahydro-3aH-[1,3]-dioxolo[4,5-e]furo[3,2-b]oxocin-8-yl)prop-2-yn-1-yl 2,4,6-triisopropylbenzenesulfonate

(4S,5S)-4-((3aR,5S,7R,8R,9aS)-5-{(S)-1-[(tert-butyldiphenylsilyl)oxy]propyl}-8-hydroxy-2,2-dimethylhexahydro-3aH-[1,3]dioxolo[4,5-d]oxocin-7-yl)-5-[(4-methoxyphenoxy)methyl]-1,3-dioxolan-2-one

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