2-[(2R,3S,4aR,6R,7S,8aR,9aS,10aS)-3-Benzyloxy-2-methyl-6-triisopropylsilanyloxy-7-(2-triisopropylsilanyloxy-ethyl)-decahydro-1,8,10-trioxa-anthracen-2-yl]-ethanol

Base Information

• Chemical Name: 2-[(2R,3S,4aR,6R,7S,8aR,9aS,10aS)-3-Benzyloxy-2-methyl-6-triisopropylsilanyloxy-7-(2-triisopropylsilanyloxy-ethyl)-decahydro-1,8,10-trioxa-anthracen-2-yl]-ethanol
• CAS No.: 647842-52-2
• Molecular Formula: C₄₁H₇₄O₇Si₂
• Molecular Weight: 735.205

Synonyms:

Chemical Property of 2-[(2R,3S,4aR,6R,7S,8aR,9aS,10aS)-3-Benzyloxy-2-methyl-6-triisopropylsilanyloxy-7-(2-triisopropylsilanyloxy-ethyl)-decahydro-1,8,10-trioxa-anthracen-2-yl]-ethanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(2R,3S,4aR,6R,7S,8aR,9aS,10aS)-3-Benzyloxy-2-methyl-6-triisopropylsilanyloxy-7-(2-triisopropylsilanyloxy-ethyl)-decahydro-1,8,10-trioxa-anthracen-2-yl]-ethanol

There total 21 articles about 2-[(2R,3S,4aR,6R,7S,8aR,9aS,10aS)-3-Benzyloxy-2-methyl-6-triisopropylsilanyloxy-7-(2-triisopropylsilanyloxy-ethyl)-decahydro-1,8,10-trioxa-anthracen-2-yl]-ethanol 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:

(2R,3S,4aR,6R,7S,8aR,9aS,10aS)-3-Benzyloxy-2-methyl-6-triisopropylsilanyloxy-7-(2-triisopropylsilanyloxy-ethyl)-2-vinyl-decahydro-1,8,10-trioxa-anthracene → 2-[(2R,3S,4aR,6R,7S,8aR,9aS,10aS)-3-Benzyloxy-2-methyl-6-triisopropylsilanyloxy-7-(2-triisopropylsilanyloxy-ethyl)-decahydro-1,8,10-trioxa-anthracen-2-yl]-ethanol (647842-52-2)

Guidance literature:

(2R,3S,4aR,6R,7S,8aR,9aS,10aS)-3-Benzyloxy-2-methyl-6-triisopropylsilanyloxy-7-(2-triisopropylsilanyloxy-ethyl)-2-vinyl-decahydro-1,8,10-trioxa-anthracene; With bis(cyclohexanyl)borane; In tetrahydrofuran; at 0 ℃;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; at 0 ℃;

DOI:10.1016/j.tetlet.2003.10.010

Reference yield:

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → 2-[(2R,3S,4aR,6R,7S,8aR,9aS,10aS)-3-Benzyloxy-2-methyl-6-triisopropylsilanyloxy-7-(2-triisopropylsilanyloxy-ethyl)-decahydro-1,8,10-trioxa-anthracen-2-yl]-ethanol (647842-52-2)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

2.1: H₂ / Pd(OH)2-C / ethyl acetate / 20 °C

3.1: 86 percent / pyridine / CH₂Cl₂ / 20 °C

4.1: dimethylsulfoxide / 50 °C

5.1: CH₂Cl₂ / Heating

6.1: DIBAL-H / CH₂Cl₂ / -78 °C

7.1: CH₂Cl₂ / Heating

8.1: 95 percent / DIBAL-H / CH₂Cl₂ / -78 °C

9.1: 90 percent / t-BuOOH; (+)-DET; 4 Angstroem MS / Ti(OiPr)4 / CH₂Cl₂ / -20 °C

10.1: SO₃*py; DMSO; Et₃N / CH₂Cl₂ / 0 °C

11.1: NaHMDS / tetrahydrofuran / 0 °C

12.1: 92 percent / TBAF / tetrahydrofuran / 20 °C

13.1: 90 percent / PPTS / CH₂Cl₂ / 20 °C

14.1: KH / tetrahydrofuran / Heating

15.1: (c-Hex)2BH / tetrahydrofuran / 0 °C

15.2: aq. H₂O₂; aq. NaOH / tetrahydrofuran / 0 °C

With pyridine; 2,6-dimethylpyridine; tert.-butylhydroperoxide; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; 4 Angstroem MS; bis(cyclohexanyl)borane; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; potassium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; titanium(IV) isopropylate; palladium hydroxide - carbon; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; ethyl acetate; 7.1: Wittig reaction / 9.1: Sharpless oxidation / 11.1: Wittig reaction;

DOI:10.1016/j.tetlet.2003.10.010

Reference yield:

(2R,4aR,6S,7R,8aS)-6-(2-Hydroxy-ethyl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol → 2-[(2R,3S,4aR,6R,7S,8aR,9aS,10aS)-3-Benzyloxy-2-methyl-6-triisopropylsilanyloxy-7-(2-triisopropylsilanyloxy-ethyl)-decahydro-1,8,10-trioxa-anthracen-2-yl]-ethanol (647842-52-2)

Guidance literature:

Multi-step reaction with 21 steps

1.1: imidazole / dimethylformamide / 0 °C

2.1: 4-methylmorpholine / CH₂Cl₂ / 20 °C

3.1: TBAF / tetrahydrofuran / 20 °C

4.1: 88 percent / SO₃*Py; DMSO; Et₃N / CH₂Cl₂ / 0 °C

5.1: 92 percent / SmI₂; MeOH / tetrahydrofuran / 0 °C

6.1: LiAlH₄ / diethyl ether / 0 °C

7.1: 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

8.1: H₂ / Pd(OH)2-C / ethyl acetate / 20 °C

9.1: 86 percent / pyridine / CH₂Cl₂ / 20 °C

10.1: dimethylsulfoxide / 50 °C

11.1: CH₂Cl₂ / Heating

12.1: DIBAL-H / CH₂Cl₂ / -78 °C

13.1: CH₂Cl₂ / Heating

14.1: 95 percent / DIBAL-H / CH₂Cl₂ / -78 °C

15.1: 90 percent / t-BuOOH; (+)-DET; 4 Angstroem MS / Ti(OiPr)4 / CH₂Cl₂ / -20 °C

16.1: SO₃*py; DMSO; Et₃N / CH₂Cl₂ / 0 °C

17.1: NaHMDS / tetrahydrofuran / 0 °C

18.1: 92 percent / TBAF / tetrahydrofuran / 20 °C

19.1: 90 percent / PPTS / CH₂Cl₂ / 20 °C

20.1: KH / tetrahydrofuran / Heating

21.1: (c-Hex)2BH / tetrahydrofuran / 0 °C

21.2: aq. H₂O₂; aq. NaOH / tetrahydrofuran / 0 °C

With 4-methyl-morpholine; pyridine; 1H-imidazole; 2,6-dimethylpyridine; methanol; tert.-butylhydroperoxide; lithium aluminium tetrahydride; samarium diiodide; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; 4 Angstroem MS; bis(cyclohexanyl)borane; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; potassium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; titanium(IV) isopropylate; palladium hydroxide - carbon; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; 5.1: Nakata cyclization / 13.1: Wittig reaction / 15.1: Sharpless oxidation / 17.1: Wittig reaction;

DOI:10.1016/j.tetlet.2003.10.010

upstream raw materials:

triisopropylsilyl trifluoromethanesulfonate

((2R,4aR,6S,7R,8aS)-7-Hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-acetic acid ethyl ester

(E)-3-[(2R,4aR,6S,7R,8aS)-6-(2-Oxo-ethyl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy]-acrylic acid ethyl ester

(2R,4aR,6S,7R,8aS)-6-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

Downstream raw materials:

{2-[5-[9-benzyloxy-8-(2-benzyloxy-ethyl)-8-methyl-2-vinyl-tetradecahydro-1,5,7,11-tetraoxa-naphthacen-3-yloxy]-3-(4-methoxy-benzyloxy)-2,6-dimethyl-6-vinyl-tetrahydro-pyran-2-yl]-ethoxy}-tert-butyl-diphenyl-silane

[6-benzyloxy-7-(2-benzyloxy-ethyl)-7-methyl-3-triisopropylsilanyloxy-decahydro-1,8,10-trioxa-anthracen-2-yl]-acetic acid 5-(4-methoxy-benzyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-2,6-dimethyl-2-vinyl-tetrahydro-pyran-3-yl ester

[6-benzyloxy-7-(2-benzyloxy-ethyl)-3-hydroxy-7-methyl-decahydro-1,8,10-trioxa-anthracen-2-yl]-acetic acid 5-(4-methoxy-benzyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-2,6-dimethyl-2-vinyl-tetrahydro-pyran-3-yl ester

[(2S,3R,4aS,6S,7R,8aS,9aR,10aR)-6-Benzyloxy-7-(2-benzyloxy-ethyl)-7-methyl-3-triisopropylsilanyloxy-decahydro-1,8,10-trioxa-anthracen-2-yl]-acetic acid

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