(2S,3R,4S,6R,8S,9S)-4-benzoyloxy-3,9-dimethyl-8-{(R)-2-[(tert-butyldimethylsilyl)-oxy]-1-propyl}-2-[(R)-3-ethyl-5-(E)-iodo-4-pentenyl]-1,7-dioxaspiro[5.5]undecane

Base Information

Chemical Name:(2S,3R,4S,6R,8S,9S)-4-benzoyloxy-3,9-dimethyl-8-{(R)-2-[(tert-butyldimethylsilyl)-oxy]-1-propyl}-2-[(R)-3-ethyl-5-(E)-iodo-4-pentenyl]-1,7-dioxaspiro[5.5]undecane
CAS No.:203063-83-6
Molecular Formula:C₃₄H₅₅IO₅Si
Molecular Weight:698.798
Hs Code.:

(2S,3R,4S,6R,8S,9S)-4-benzoyloxy-3,9-dimethyl-8-{(R)-2-[(tert-butyldimethylsilyl)-oxy]-1-propyl}-2-[(R)-3-ethyl-5-(E)-iodo-4-pentenyl]-1,7-dioxaspiro[5.5]undecane

Synonyms:(2S,3R,4S,6R,8S,9S)-4-benzoyloxy-3,9-dimethyl-8-{(R)-2-[(tert-butyldimethylsilyl)-oxy]-1-propyl}-2-[(R)-3-ethyl-5-(E)-iodo-4-pentenyl]-1,7-dioxaspiro[5.5]undecane

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Chemical Property of (2S,3R,4S,6R,8S,9S)-4-benzoyloxy-3,9-dimethyl-8-{(R)-2-[(tert-butyldimethylsilyl)-oxy]-1-propyl}-2-[(R)-3-ethyl-5-(E)-iodo-4-pentenyl]-1,7-dioxaspiro[5.5]undecane

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Technology Process of (2S,3R,4S,6R,8S,9S)-4-benzoyloxy-3,9-dimethyl-8-{(R)-2-[(tert-butyldimethylsilyl)-oxy]-1-propyl}-2-[(R)-3-ethyl-5-(E)-iodo-4-pentenyl]-1,7-dioxaspiro[5.5]undecane

There total 19 articles about (2S,3R,4S,6R,8S,9S)-4-benzoyloxy-3,9-dimethyl-8-{(R)-2-[(tert-butyldimethylsilyl)-oxy]-1-propyl}-2-[(R)-3-ethyl-5-(E)-iodo-4-pentenyl]-1,7-dioxaspiro[5.5]undecane 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: 76.0%

: 75-47-8
iodoform

: 203063-82-5
(2S,3R,4S,6R,8S,9S)-4-benzoyloxy-3,9-dimethyl-8-{(R)-2-[(tert-butyldimethyl-silyl)oxy]-1-propyl}-2-[(R)-3-ethyl-3-formylpropyl]-1,7-dioxaspiro[5.5]undecane

: 203063-83-6
(2S,3R,4S,6R,8S,9S)-4-benzoyloxy-3,9-dimethyl-8-{(R)-2-[(tert-butyldimethylsilyl)-oxy]-1-propyl}-2-[(R)-3-ethyl-5-(E)-iodo-4-pentenyl]-1,7-dioxaspiro[5.5]undecane

Guidance literature:: With chromium dichloride; In tetrahydrofuran; at 0 ℃;
DOI:10.1039/a707251a

Reference yield: 76.0%

: 75-47-8
iodoform

: 203063-82-5
(2S,3R,4S,6R,8S,9S)-4-benzoyloxy-3,9-dimethyl-8-{(R)-2-[(tert-butyldimethyl-silyl)oxy]-1-propyl}-2-[(R)-3-ethyl-3-formylpropyl]-1,7-dioxaspiro[5.5]undecane

: (2S,3R,4S,6R,8S,9S)-4-benzoyloxy-3,9-dimethyl-8-{(R)-2-[(tert-butyldimethylsilyl)-oxy]-1-propyl}-2-[(R)-3-ethyl-5-(Z)-iodo-4-pentenyl]-1,7-dioxaspiro[5.5]undecane

: 203063-83-6
(2S,3R,4S,6R,8S,9S)-4-benzoyloxy-3,9-dimethyl-8-{(R)-2-[(tert-butyldimethylsilyl)-oxy]-1-propyl}-2-[(R)-3-ethyl-5-(E)-iodo-4-pentenyl]-1,7-dioxaspiro[5.5]undecane

Guidance literature:: With chromium dichloride; In tetrahydrofuran; at 0 - 20 ℃; for 3h;
DOI:10.1021/jo0104429

Reference yield:

: 131725-13-8
(2S,3S,4S,6R,8S,9S)-3,9-dimethyl-8-[(R)-2-hydroxy-1-propyl]-2-[(R)-3-(hydroxymethyl)-1-pentyl]-1,7-dioxaspiro[5.5]undecan-4-ol

: 203063-83-6
(2S,3R,4S,6R,8S,9S)-4-benzoyloxy-3,9-dimethyl-8-{(R)-2-[(tert-butyldimethylsilyl)-oxy]-1-propyl}-2-[(R)-3-ethyl-5-(E)-iodo-4-pentenyl]-1,7-dioxaspiro[5.5]undecane

Guidance literature:: Multi-step reaction with 5 steps

1: 13 mg / 2,6-lutidine / CH₂Cl₂ / 2.5 h / -78 °C

2: 90 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 3 h

3: 44 percent / hydrofluoric acid*pyridine / tetrahydrofuran; pyridine / 11 h / 20 °C

4: 96 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / 2.33 h / -78 - 20 °C

5: 76 percent / chromium(II) chloride / tetrahydrofuran / 3 h / 0 - 20 °C

With 2,6-dimethylpyridine; chromium dichloride; dmap; oxalyl dichloride; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; pyridine; dichloromethane; 4: Swern oxidation / 5: Takai reaction;
DOI:10.1021/jo0104429