(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

Base Information

• Chemical Name: (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
• CAS No.: 1439511-39-3
• Molecular Formula: C₃₃H₅₀O₈S
• Molecular Weight: 606.821

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 26 articles about (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 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: 84.0%

2,4,6-triisopropylphenylsulfonyl chloride (6553-96-4) + (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-ol (1439511-32-6) → (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 (1439511-39-3)

Guidance literature:

With dmap; In dichloromethane; at -30 - -20 ℃; for 2h; Inert atmosphere;

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) → (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 (1439511-39-3)

Guidance literature:

Multi-step reaction with 19 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

10.1: pyridinium p-toluenesulfonate / dichloromethane / 11 h / 20 °C / Inert atmosphere

11.1: triethylamine / dichloromethane / 0.17 h / 20 °C / Inert atmosphere

12.1: potassium carbonate / methanol / 0.5 h / 20 °C / Inert atmosphere

13.1: potassium tert-butylate / tetrahydrofuran / 0.17 h / -78 - 20 °C / Inert atmosphere

13.2: 0.17 h / 20 °C / Inert atmosphere

14.1: sodium hydrogencarbonate; ammonium cerium (IV) nitrate / acetonitrile; water / 0.25 h / -10 °C

15.1: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / toluene / 0.25 h / 100 °C / Inert atmosphere

16.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 0.67 h / 20 °C / Inert atmosphere

17.1: diethyl ether; hexane; tetrahydrofuran / 0.17 h / -78 - 20 °C / Inert atmosphere

18.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 50 °C / Inert atmosphere

19.1: dmap / dichloromethane / 2 h / -30 - -20 °C / Inert atmosphere

With 2,6-dimethylpyridine; chromium dichloride; dmap; 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; osmium(VIII) oxide; ammonium cerium (IV) nitrate; potassium hexacyanoperferrate; 2,2'-azobis(isobutyronitrile); methanesulfonamide; dimethylsulfide borane complex; potassium tert-butylate; tetrabutyl ammonium fluoride; water; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; acetic acid; hydroquinidein 1,4-phthalazinediyl diether; triethylamine; nickel dichloride; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 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 / 15.1: |Barton-McCombie Deoxygenation / 16.1: |Dess-Martin Oxidation;

DOI:10.1021/ol401231y

Reference yield:

[(4S,5R)-5-ethynyl-2,2-dimethyl-1,3-dioxolan-4-yl]methanol (127305-55-9) → (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 (1439511-39-3)

Guidance literature:

Multi-step reaction with 22 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

13.1: pyridinium p-toluenesulfonate / dichloromethane / 11 h / 20 °C / Inert atmosphere

14.1: triethylamine / dichloromethane / 0.17 h / 20 °C / Inert atmosphere

15.1: potassium carbonate / methanol / 0.5 h / 20 °C / Inert atmosphere

16.1: potassium tert-butylate / tetrahydrofuran / 0.17 h / -78 - 20 °C / Inert atmosphere

16.2: 0.17 h / 20 °C / Inert atmosphere

17.1: sodium hydrogencarbonate; ammonium cerium (IV) nitrate / acetonitrile; water / 0.25 h / -10 °C

18.1: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / toluene / 0.25 h / 100 °C / Inert atmosphere

19.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 0.67 h / 20 °C / Inert atmosphere

20.1: diethyl ether; hexane; tetrahydrofuran / 0.17 h / -78 - 20 °C / Inert atmosphere

21.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 50 °C / Inert atmosphere

22.1: dmap / dichloromethane / 2 h / -30 - -20 °C / Inert atmosphere

With pyridine; 2,6-dimethylpyridine; chromium dichloride; dmap; 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; N-iodo-succinimide; osmium(VIII) oxide; ammonium cerium (IV) nitrate; potassium hexacyanoperferrate; 2,2'-azobis(isobutyronitrile); methanesulfonamide; dimethylsulfide borane complex; potassium tert-butylate; tetrabutyl ammonium fluoride; water; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; silver nitrate; acetic acid; hydroquinidein 1,4-phthalazinediyl diether; triethylamine; triphenylphosphine; nickel dichloride; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; hexane; 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 / 18.1: |Barton-McCombie Deoxygenation / 19.1: |Dess-Martin Oxidation;

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

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

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