(Z)-(2R,4aR,6S,11aS)-6-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-phenyl-4a,8,11,11a-tetrahydro-4H-1,3,5-trioxa-benzocyclononen-7-one

Base Information

• Chemical Name: (Z)-(2R,4aR,6S,11aS)-6-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-phenyl-4a,8,11,11a-tetrahydro-4H-1,3,5-trioxa-benzocyclononen-7-one
• CAS No.: 193970-45-5
• Molecular Formula: C₂₄H₃₆O₅Si
• Molecular Weight: 432.632

Synonyms:(Z)-(2R,4aR,6S,11aS)-6-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-phenyl-4a,8,11,11a-tetrahydro-4H-1,3,5-trioxa-benzocyclononen-7-one

Chemical Property of (Z)-(2R,4aR,6S,11aS)-6-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-phenyl-4a,8,11,11a-tetrahydro-4H-1,3,5-trioxa-benzocyclononen-7-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-(2R,4aR,6S,11aS)-6-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-phenyl-4a,8,11,11a-tetrahydro-4H-1,3,5-trioxa-benzocyclononen-7-one

There total 16 articles about (Z)-(2R,4aR,6S,11aS)-6-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-phenyl-4a,8,11,11a-tetrahydro-4H-1,3,5-trioxa-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: 96.0%

(Z)-(2R,4aR,11aS)-6-[2-(tert-Butyl-dimethyl-silanyloxy)-eth-(E)-ylidene]-2-phenyl-4a,8,11,11a-tetrahydro-4H-1,3,5-trioxa-benzocyclononen-7-one (193970-43-3) → (Z)-(2R,4aR,6S,11aS)-6-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-phenyl-4a,8,11,11a-tetrahydro-4H-1,3,5-trioxa-benzocyclononen-7-one (193970-45-5)

Guidance literature:

With hydrido(triphenylphosphine)copper(I) hexamer; In benzene; at 25 ℃; for 3h;

Reference yield:

2-deoxy-D-ribose (22900-10-3,35536-75-5,36792-85-5,113890-34-9,113890-37-2,133813-23-7) → (Z)-(2R,4aR,6S,11aS)-6-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-phenyl-4a,8,11,11a-tetrahydro-4H-1,3,5-trioxa-benzocyclononen-7-one (193970-45-5)

Guidance literature:

Multi-step reaction with 17 steps

1: dimethylformamide / 15 h / 25 °C

2: dimethylformamide / 15 h / 25 °C

3: 90 percent / imidazole / CH₂Cl₂ / 12 h / 25 °C

4: 1.) O₃, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 10 min, 2.) CH₂Cl₂, 25 deg C, 3 h

5: 1.) LiHMDS / 1.) toluene, THF, 0 deg C, 20 min, 2.) toluene, THF, 0 deg C, 1 h; 25 deg C, 7 h

6: 82 percent / TBAF / tetrahydrofuran / 7 h / 25 °C

7: 87 percent / Dess-Martin reagent / CH₂Cl₂ / 4.5 h / 25 °C

8: 96 percent / NaClO₂, NaH₂PO₄, 2-methyl-2-butene, H₂O / tetrahydrofuran; 2-methyl-propan-2-ol / 3 h / 25 °C

9: Et₃N / tetrahydrofuran / 0.33 h / 0 °C

10: DMAP / tetrahydrofuran; benzene / 1 h / 80 °C

11: 90 percent / KHMDS, HMPA / tetrahydrofuran; toluene / 1 h / -78 °C

12: 95 percent / LiCl / Pd(Ph₃P)4 / tetrahydrofuran / 1.5 h / 80 °C

13: 72 percent / O₂, meso-tetraphenylporphyrin / CCl₄ / 3 h / 25 °C / Irradiation

14: 99 percent / H₂ / Lindlar catalyst / methanol / 0.33 h / 25 °C

15: 93 percent / imidazole / CH₂Cl₂ / 0.5 h / 25 °C

16: 85 percent / NMO, tetrapropylammonium perruthenate / CH₂Cl₂ / 1 h / 25 °C

17: 96 percent / <(Ph₃P)CuH>6 / benzene / 3 h / 25 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium chlorite; sodium dihydrogenphosphate; 5,10,15,20-tetrakisphenylporphyrin; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; hydrido(triphenylphosphine)copper(I) hexamer; tetrabutyl ammonium fluoride; water; hydrogen; oxygen; potassium hexamethylsilazane; Dess-Martin periodane; ozone; triethylamine; triphenylphosphine; lithium chloride; lithium hexamethyldisilazane; Lindlar's catalyst; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; benzene;

Reference yield:

methyl (E,5S,6R)-5,6,7-trihydroxyhept-2-enoate (78606-78-7) → (Z)-(2R,4aR,6S,11aS)-6-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-phenyl-4a,8,11,11a-tetrahydro-4H-1,3,5-trioxa-benzocyclononen-7-one (193970-45-5)

Guidance literature:

Multi-step reaction with 16 steps

1: dimethylformamide / 15 h / 25 °C

2: 90 percent / imidazole / CH₂Cl₂ / 12 h / 25 °C

3: 1.) O₃, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 10 min, 2.) CH₂Cl₂, 25 deg C, 3 h

4: 1.) LiHMDS / 1.) toluene, THF, 0 deg C, 20 min, 2.) toluene, THF, 0 deg C, 1 h; 25 deg C, 7 h

5: 82 percent / TBAF / tetrahydrofuran / 7 h / 25 °C

6: 87 percent / Dess-Martin reagent / CH₂Cl₂ / 4.5 h / 25 °C

7: 96 percent / NaClO₂, NaH₂PO₄, 2-methyl-2-butene, H₂O / tetrahydrofuran; 2-methyl-propan-2-ol / 3 h / 25 °C

8: Et₃N / tetrahydrofuran / 0.33 h / 0 °C

9: DMAP / tetrahydrofuran; benzene / 1 h / 80 °C

10: 90 percent / KHMDS, HMPA / tetrahydrofuran; toluene / 1 h / -78 °C

11: 95 percent / LiCl / Pd(Ph₃P)4 / tetrahydrofuran / 1.5 h / 80 °C

12: 72 percent / O₂, meso-tetraphenylporphyrin / CCl₄ / 3 h / 25 °C / Irradiation

13: 99 percent / H₂ / Lindlar catalyst / methanol / 0.33 h / 25 °C

14: 93 percent / imidazole / CH₂Cl₂ / 0.5 h / 25 °C

15: 85 percent / NMO, tetrapropylammonium perruthenate / CH₂Cl₂ / 1 h / 25 °C

16: 96 percent / <(Ph₃P)CuH>6 / benzene / 3 h / 25 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium chlorite; sodium dihydrogenphosphate; 5,10,15,20-tetrakisphenylporphyrin; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; hydrido(triphenylphosphine)copper(I) hexamer; tetrabutyl ammonium fluoride; water; hydrogen; oxygen; potassium hexamethylsilazane; Dess-Martin periodane; ozone; triethylamine; triphenylphosphine; lithium chloride; lithium hexamethyldisilazane; Lindlar's catalyst; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; benzene;

upstream raw materials:

(Z)-(2R,4aR,11aS)-6-[2-(tert-Butyl-dimethyl-silanyloxy)-eth-(E)-ylidene]-2-phenyl-4a,8,11,11a-tetrahydro-4H-1,3,5-trioxa-benzocyclononen-7-one

2-deoxy-D-ribose

methyl (E,5S,6R)-5,6,7-trihydroxyhept-2-enoate

[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-acetaldehyde

Downstream raw materials:

(Z)-(1S,3R,6R,8S,13R)-15,15-Dimethyl-6-phenyl-2,5,7,14,16-pentaoxa-tricyclo[11.5.0.0^3,8]octadec-10-ene

2,2-Dimethyl-propionic acid (Z)-(2R,4aR,6S,7R,11aS)-6-(2-iodo-ethyl)-2-phenyl-4a,6,7,8,11,11a-hexahydro-4H-1,3,5-trioxa-benzocyclononen-7-yl ester

2,2-Dimethyl-propionic acid (Z)-(2R,4aR,6S,7R,11aS)-6-(2-hydroxy-ethyl)-2-phenyl-4a,6,7,8,11,11a-hexahydro-4H-1,3,5-trioxa-benzocyclononen-7-yl ester

2,2-Dimethyl-propionic acid (Z)-(2R,4aR,6S,7R,11aS)-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-phenyl-4a,6,7,8,11,11a-hexahydro-4H-1,3,5-trioxa-benzocyclononen-7-yl ester

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