(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

Base Information

Chemical Name:(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
CAS No.:1439511-25-7
Molecular Formula:C₃₂H₄₆O₆Si
Molecular Weight:554.799
Hs Code.:

Synonyms:(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

Suppliers and Price of (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

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 0 raw suppliers

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of (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

There total 22 articles about (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 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:

: C₃₄H₄₈O₇S₂Si

: 1439511-25-7
(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

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 100 ℃; for 0.25h; 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

: 1439511-25-7
(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

Guidance literature:: Multi-step reaction with 15 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

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; 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; 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;
DOI:10.1021/ol401231y

Reference yield:

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

: 1439511-25-7
(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

Guidance literature:: Multi-step reaction with 18 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

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; water; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; silver nitrate; acetic acid; hydroquinidein 1,4-phthalazinediyl diether; triethylamine; 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 / 18.1: |Barton-McCombie Deoxygenation;
DOI:10.1021/ol401231y