(Z)-(4aS,6R,11aR)-6-[(R)-2-Benzyloxy-2-((2R,3R,6S)-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yl)-ethyl]-3,4,4a,8,11,11a-hexahydro-2H-1,5-dioxa-benzocyclononen-7-one

Base Information

Chemical Name:(Z)-(4aS,6R,11aR)-6-[(R)-2-Benzyloxy-2-((2R,3R,6S)-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yl)-ethyl]-3,4,4a,8,11,11a-hexahydro-2H-1,5-dioxa-benzocyclononen-7-one
CAS No.:419549-48-7
Molecular Formula:C₃₃H₄₂O₇
Molecular Weight:550.692
Hs Code.:

(Z)-(4aS,6R,11aR)-6-[(R)-2-Benzyloxy-2-((2R,3R,6S)-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yl)-ethyl]-3,4,4a,8,11,11a-hexahydro-2H-1,5-dioxa-benzocyclononen-7-one

Synonyms:(Z)-(4aS,6R,11aR)-6-[(R)-2-Benzyloxy-2-((2R,3R,6S)-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yl)-ethyl]-3,4,4a,8,11,11a-hexahydro-2H-1,5-dioxa-benzocyclononen-7-one

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Chemical Property of (Z)-(4aS,6R,11aR)-6-[(R)-2-Benzyloxy-2-((2R,3R,6S)-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yl)-ethyl]-3,4,4a,8,11,11a-hexahydro-2H-1,5-dioxa-benzocyclononen-7-one

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Technology Process of (Z)-(4aS,6R,11aR)-6-[(R)-2-Benzyloxy-2-((2R,3R,6S)-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yl)-ethyl]-3,4,4a,8,11,11a-hexahydro-2H-1,5-dioxa-benzocyclononen-7-one

There total 18 articles about (Z)-(4aS,6R,11aR)-6-[(R)-2-Benzyloxy-2-((2R,3R,6S)-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yl)-ethyl]-3,4,4a,8,11,11a-hexahydro-2H-1,5-dioxa-benzocyclononen-7-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: 100.0%

: 419549-24-9
Acetic acid (2S,3R,6S)-6-benzyloxymethyl-2-[(R)-1-benzyloxy-2-((Z)-(4aS,6R,11aR)-7-oxo-3,4,4a,6,7,8,11,11a-octahydro-2H-1,5-dioxa-benzocyclononen-6-yl)-ethyl]-tetrahydro-pyran-3-yl ester

: 419549-48-7
(Z)-(4aS,6R,11aR)-6-[(R)-2-Benzyloxy-2-((2R,3R,6S)-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yl)-ethyl]-3,4,4a,8,11,11a-hexahydro-2H-1,5-dioxa-benzocyclononen-7-one

Guidance literature:: With potassium carbonate; In methanol;
DOI:10.1021/jo034021y

Reference yield:

: [5-(tert-butyl-diphenyl-silanyloxy)-6-ethynyl-5,6-dihydro-2H-pyran-2-yl]-methanol

: 419549-48-7
(Z)-(4aS,6R,11aR)-6-[(R)-2-Benzyloxy-2-((2R,3R,6S)-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yl)-ethyl]-3,4,4a,8,11,11a-hexahydro-2H-1,5-dioxa-benzocyclononen-7-one

Guidance literature:: Multi-step reaction with 14 steps

1.1: 87 percent / KOH / 2 h / 90 °C

2.1: n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C

2.2: 55 percent / tetrahydrofuran; hexane / 17 h / -78 - 0 °C

3.1: 95 percent / Red-Al(R) / tetrahydrofuran; toluene / 0.58 h / 0 - 20 °C

4.1: m-chloroperbenzoic acid; di-sodium hydrogenphosphate / CH₂Cl₂ / 14 h / 20 °C

5.1: 1.92 g / Red-Al(R) / toluene / 1.5 h / 0 °C

6.1: H₂; sodium hydrogen carbonate / Pd/C / ethanol / 4 h / 20 °C

7.1: 10-camphorsulfonic acid / CH₂Cl₂ / 14 h / 20 °C

7.2: 525 mg / BH₃*THF / tetrahydrofuran / 7 h / Heating

8.1: 92 percent / IBX / dimethylsulfoxide / 5 h / 20 °C

9.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

9.2: 86 percent / tetrahydrofuran; hexane / 0.58 h / -78 °C

10.1: TBAF / tetrahydrofuran / 7 h / 20 °C

11.1: 201 mg / DMAP; pyridine / CH₂Cl₂ / 2 h / 20 °C

12.1: pyridinium p-toluenesulfonate / methanol / 0.5 h / 20 °C

13.1: Co₂(CO)8 / CH₂Cl₂ / 1.5 h / 20 °C

13.2: BF₃*Et₂O / CH₂Cl₂; 1,2-dichloro-ethane / 0.67 h / 0 - 20 °C

13.3: 7.3 mg / H₂ / benzene / 4.5 h / 65 °C / 73557.6 Torr

14.1: 99 percent / K₂CO₃ / methanol / 3 h / 20 °C

With pyridine; dmap; potassium hydroxide; disodium hydrogenphosphate; n-butyllithium; dicobalt octacarbonyl; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; dimethyl sulfoxide; toluene;
DOI:10.1021/ol0256264

Reference yield:

: (6-benzyloxymethyl-2-ethynyl-3,6-dihydro-2H-pyran-3-yloxy)-tert-butyl-diphenyl-silane

: 419549-48-7
(Z)-(4aS,6R,11aR)-6-[(R)-2-Benzyloxy-2-((2R,3R,6S)-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yl)-ethyl]-3,4,4a,8,11,11a-hexahydro-2H-1,5-dioxa-benzocyclononen-7-one

Guidance literature:: Multi-step reaction with 13 steps

1.1: n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C

1.2: 55 percent / tetrahydrofuran; hexane / 17 h / -78 - 0 °C

2.1: 95 percent / Red-Al(R) / tetrahydrofuran; toluene / 0.58 h / 0 - 20 °C

3.1: m-chloroperbenzoic acid; di-sodium hydrogenphosphate / CH₂Cl₂ / 14 h / 20 °C

4.1: 1.92 g / Red-Al(R) / toluene / 1.5 h / 0 °C

5.1: H₂; sodium hydrogen carbonate / Pd/C / ethanol / 4 h / 20 °C

6.1: 10-camphorsulfonic acid / CH₂Cl₂ / 14 h / 20 °C

6.2: 525 mg / BH₃*THF / tetrahydrofuran / 7 h / Heating

7.1: 92 percent / IBX / dimethylsulfoxide / 5 h / 20 °C

8.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

8.2: 86 percent / tetrahydrofuran; hexane / 0.58 h / -78 °C

9.1: TBAF / tetrahydrofuran / 7 h / 20 °C

10.1: 201 mg / DMAP; pyridine / CH₂Cl₂ / 2 h / 20 °C

11.1: pyridinium p-toluenesulfonate / methanol / 0.5 h / 20 °C

12.1: Co₂(CO)8 / CH₂Cl₂ / 1.5 h / 20 °C

12.2: BF₃*Et₂O / CH₂Cl₂; 1,2-dichloro-ethane / 0.67 h / 0 - 20 °C

12.3: 7.3 mg / H₂ / benzene / 4.5 h / 65 °C / 73557.6 Torr

13.1: 99 percent / K₂CO₃ / methanol / 3 h / 20 °C

With pyridine; dmap; disodium hydrogenphosphate; n-butyllithium; dicobalt octacarbonyl; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; dimethyl sulfoxide; toluene;
DOI:10.1021/ol0256264