[(2R,3S,3aR,4aS,7R,8aS,9S,9aR)-2-((E)-4-{(2S,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-methylene-tetrahydro-furan-2-yl}-2-methoxy-but-1-enyl)-3,9-bis-triethylsilanyloxy-decahydro-furo[3,2-b]pyrano[2,3-e]pyran-7-yl]-acetic acid methyl ester

Base Information

• Chemical Name: [(2R,3S,3aR,4aS,7R,8aS,9S,9aR)-2-((E)-4-{(2S,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-methylene-tetrahydro-furan-2-yl}-2-methoxy-but-1-enyl)-3,9-bis-triethylsilanyloxy-decahydro-furo[3,2-b]pyrano[2,3-e]pyran-7-yl]-acetic acid methyl ester
• CAS No.: 870700-31-5
• Molecular Formula: C₅₃H₈₄O₁₀Si₃
• Molecular Weight: 965.5
• Mol file: 870700-31-5.mol

Synonyms:[(2R,3S,3aR,4aS,7R,8aS,9S,9aR)-2-((E)-4-{(2S,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-methylene-tetrahydro-furan-2-yl}-2-methoxy-but-1-enyl)-3,9-bis-triethylsilanyloxy-decahydro-furo[3,2-b]pyrano[2,3-e]pyran-7-yl]-acetic acid methyl ester

Chemical Property of [(2R,3S,3aR,4aS,7R,8aS,9S,9aR)-2-((E)-4-{(2S,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-methylene-tetrahydro-furan-2-yl}-2-methoxy-but-1-enyl)-3,9-bis-triethylsilanyloxy-decahydro-furo[3,2-b]pyrano[2,3-e]pyran-7-yl]-acetic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2R,3S,3aR,4aS,7R,8aS,9S,9aR)-2-((E)-4-{(2S,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-methylene-tetrahydro-furan-2-yl}-2-methoxy-but-1-enyl)-3,9-bis-triethylsilanyloxy-decahydro-furo[3,2-b]pyrano[2,3-e]pyran-7-yl]-acetic acid methyl ester

There total 18 articles about [(2R,3S,3aR,4aS,7R,8aS,9S,9aR)-2-((E)-4-{(2S,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-methylene-tetrahydro-furan-2-yl}-2-methoxy-but-1-enyl)-3,9-bis-triethylsilanyloxy-decahydro-furo[3,2-b]pyrano[2,3-e]pyran-7-yl]-acetic acid methyl ester 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:

2,2-Dimethyl-propionic acid (2R,3S,3aR,5S,6R,6aR)-3,6-bis-(tert-butyl-diphenyl-silanyloxy)-5-triethylsilanyloxy-hexahydro-furo[3,2-b]furan-2-ylmethyl ester (870700-43-9) → [(2R,3S,3aR,4aS,7R,8aS,9S,9aR)-2-((E)-4-{(2S,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-methylene-tetrahydro-furan-2-yl}-2-methoxy-but-1-enyl)-3,9-bis-triethylsilanyloxy-decahydro-furo[3,2-b]pyrano[2,3-e]pyran-7-yl]-acetic acid methyl ester (870700-31-5)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 875 mg / HCl / CH₂Cl₂; methanol / 0.25 h / 0 °C

2.1: KOtBu / tetrahydrofuran / 0.17 h / 0 °C

2.2: tetrahydrofuran / 0 - 20 °C

2.3: 87 percent / aq. KOH / tetrahydrofuran / 0.5 h

3.1: 73 percent / N-methylmorpholine N-oxide; water / OsO₄ / acetone; 2-methyl-propan-2-ol / 24 h / 20 °C

4.1: 35 percent / TMSOTf / cyclohexane / 0.5 h / 0 °C

5.1: 86 percent / BF₃*OEt₂ / acetonitrile / 16 h / 60 °C

6.1: TBAF; AcOH / tetrahydrofuran / 24 h / 20 °C

7.1: 1.88 g / Amberlist IRA-400; methanol / 1 h / 20 °C

8.1: DBU / benzene / 16 h / Heating

9.1: 93 percent / Amberlist IRA-400; methanol / 24 h / Heating

10.1: 91 percent / imidazole / dimethylformamide / 2 h / 20 °C

11.1: 89 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -50 - 20 °C

12.1: tetrahydrofuran; hexane / -78 - 20 °C / ----------------

With 1H-imidazole; hydrogenchloride; methanol; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; Amberlist IRA-400; boron trifluoride diethyl etherate; potassium tert-butylate; tetrabutyl ammonium fluoride; water; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; osmium(VIII) oxide; In tetrahydrofuran; methanol; hexane; dichloromethane; cyclohexane; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol; benzene; 2.2: Wittig reaction / 8.1: Michael addition / 11.1: Swern oxidation / 12.1: Wittig reaction;

DOI:10.1021/jo051479m

Reference yield:

(3R,3aR,6R,6aR)-3,6-Bis-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-tetrahydro-furo[3,2-b]furan-2-one (502687-20-9) → [(2R,3S,3aR,4aS,7R,8aS,9S,9aR)-2-((E)-4-{(2S,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-methylene-tetrahydro-furan-2-yl}-2-methoxy-but-1-enyl)-3,9-bis-triethylsilanyloxy-decahydro-furo[3,2-b]pyrano[2,3-e]pyran-7-yl]-acetic acid methyl ester (870700-31-5)

Guidance literature:

Multi-step reaction with 16 steps

1.1: 11.5 g / imidazole / dimethylformamide / 0.5 h / 0 °C

2.1: 100 percent / toluene; tetrahydrofuran / 3 h / 90 °C

3.1: BH₃*SMe₂ / tetrahydrofuran / 0.75 h / 0 - 20 °C

3.2: 70 percent / H₂O₂; NaOH / tetrahydrofuran; H₂O / 0 - 20 °C

4.1: 87 percent / DMAP; Et₃N / CH₂Cl₂ / 3 h / 20 °C

5.1: 875 mg / HCl / CH₂Cl₂; methanol / 0.25 h / 0 °C

6.1: KOtBu / tetrahydrofuran / 0.17 h / 0 °C

6.2: tetrahydrofuran / 0 - 20 °C

6.3: 87 percent / aq. KOH / tetrahydrofuran / 0.5 h

7.1: 73 percent / N-methylmorpholine N-oxide; water / OsO₄ / acetone; 2-methyl-propan-2-ol / 24 h / 20 °C

8.1: 35 percent / TMSOTf / cyclohexane / 0.5 h / 0 °C

9.1: 86 percent / BF₃*OEt₂ / acetonitrile / 16 h / 60 °C

10.1: TBAF; AcOH / tetrahydrofuran / 24 h / 20 °C

11.1: 1.88 g / Amberlist IRA-400; methanol / 1 h / 20 °C

12.1: DBU / benzene / 16 h / Heating

13.1: 93 percent / Amberlist IRA-400; methanol / 24 h / Heating

14.1: 91 percent / imidazole / dimethylformamide / 2 h / 20 °C

15.1: 89 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -50 - 20 °C

16.1: tetrahydrofuran; hexane / -78 - 20 °C / ----------------

With 1H-imidazole; hydrogenchloride; methanol; dmap; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; dimethylsulfide borane complex; Amberlist IRA-400; boron trifluoride diethyl etherate; potassium tert-butylate; tetrabutyl ammonium fluoride; water; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; osmium(VIII) oxide; In tetrahydrofuran; methanol; hexane; dichloromethane; cyclohexane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; tert-butyl alcohol; benzene; 6.2: Wittig reaction / 12.1: Michael addition / 15.1: Swern oxidation / 16.1: Wittig reaction;

DOI:10.1021/jo051479m

Reference yield:

(3R,3aR,5S,6R,6aR)-3,6-Bis-(tert-butyl-diphenyl-silanyloxy)-2-methylene-5-triethylsilanyloxy-hexahydro-furo[3,2-b]furan (502687-21-0) → [(2R,3S,3aR,4aS,7R,8aS,9S,9aR)-2-((E)-4-{(2S,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-methylene-tetrahydro-furan-2-yl}-2-methoxy-but-1-enyl)-3,9-bis-triethylsilanyloxy-decahydro-furo[3,2-b]pyrano[2,3-e]pyran-7-yl]-acetic acid methyl ester (870700-31-5)

Guidance literature:

Multi-step reaction with 14 steps

1.1: BH₃*SMe₂ / tetrahydrofuran / 0.75 h / 0 - 20 °C

1.2: 70 percent / H₂O₂; NaOH / tetrahydrofuran; H₂O / 0 - 20 °C

2.1: 87 percent / DMAP; Et₃N / CH₂Cl₂ / 3 h / 20 °C

3.1: 875 mg / HCl / CH₂Cl₂; methanol / 0.25 h / 0 °C

4.1: KOtBu / tetrahydrofuran / 0.17 h / 0 °C

4.2: tetrahydrofuran / 0 - 20 °C

4.3: 87 percent / aq. KOH / tetrahydrofuran / 0.5 h

5.1: 73 percent / N-methylmorpholine N-oxide; water / OsO₄ / acetone; 2-methyl-propan-2-ol / 24 h / 20 °C

6.1: 35 percent / TMSOTf / cyclohexane / 0.5 h / 0 °C

7.1: 86 percent / BF₃*OEt₂ / acetonitrile / 16 h / 60 °C

8.1: TBAF; AcOH / tetrahydrofuran / 24 h / 20 °C

9.1: 1.88 g / Amberlist IRA-400; methanol / 1 h / 20 °C

10.1: DBU / benzene / 16 h / Heating

11.1: 93 percent / Amberlist IRA-400; methanol / 24 h / Heating

12.1: 91 percent / imidazole / dimethylformamide / 2 h / 20 °C

13.1: 89 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -50 - 20 °C

14.1: tetrahydrofuran; hexane / -78 - 20 °C / ----------------

With 1H-imidazole; hydrogenchloride; methanol; dmap; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; dimethylsulfide borane complex; Amberlist IRA-400; boron trifluoride diethyl etherate; potassium tert-butylate; tetrabutyl ammonium fluoride; water; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; osmium(VIII) oxide; In tetrahydrofuran; methanol; hexane; dichloromethane; cyclohexane; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol; benzene; 4.2: Wittig reaction / 10.1: Michael addition / 13.1: Swern oxidation / 14.1: Wittig reaction;

DOI:10.1021/jo051479m

upstream raw materials:

((2S,3R,3aR,4aS,7R,8aS,9S,9aR)-2-Formyl-3,9-bis-triethylsilanyloxy-decahydro-furo[3,2-b]pyrano[2,3-e]pyran-7-yl)-acetic acid methyl ester

2,2-Dimethyl-propionic acid (2R,3S,3aR,5S,6R,6aR)-3,6-bis-(tert-butyl-diphenyl-silanyloxy)-5-triethylsilanyloxy-hexahydro-furo[3,2-b]furan-2-ylmethyl ester

2,2-Dimethyl-propionic acid (2R,3S,3aR,5R,6R,7R,7aR)-5,6-diacetoxy-3,7-bis-(tert-butyl-diphenyl-silanyloxy)-hexahydro-furo[3,2-b]pyran-2-ylmethyl ester

3-trimethylsilylpent-4-enoic acid methyl ester