[(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

Base Information

• Chemical Name: [(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
• CAS No.: 1055039-96-7
• Molecular Formula: C₃₉H₅₈O₈Si
• Molecular Weight: 682.97
• Mol file: 1055039-96-7.mol

Synonyms:

Chemical Property of [(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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(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

There total 24 articles about [(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 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:

[(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]-acetaldehyde → [(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 (1055039-96-7)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In tetrahydrofuran; water; tert-butyl alcohol; at 20 ℃;

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 → [(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 (1055039-96-7)

Guidance literature:

Multi-step reaction with 25 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

22.1: KH / tetrahydrofuran / Heating

23.1: CSA / methanol; CH₂Cl₂ / 0 - 20 °C

24.1: TEMPO; NaClO; KBr / CH₂Cl₂; H₂O / 0 °C

25.1: NaClO₂; 2-methyl-2-butene; NaH₂PO₄ / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 20 °C

With 4-methyl-morpholine; pyridine; 1H-imidazole; 2,6-dimethylpyridine; methanol; tert.-butylhydroperoxide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; samarium diiodide; 2-methyl-but-2-ene; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; 4 Angstroem MS; camphor-10-sulfonic acid; bis(cyclohexanyl)borane; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; potassium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; potassium bromide; titanium(IV) isopropylate; palladium hydroxide - carbon; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; 5.1: Nakata cyclization / 13.1: Wittig reaction / 15.1: Sharpless oxidation / 17.1: Wittig reaction;

DOI:10.1016/j.tetlet.2003.10.010

Reference yield:

((2R,4aR,6S,7R,8aS)-7-Hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-acetic acid ethyl ester (647842-39-5) → [(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 (1055039-96-7)

Guidance literature:

Multi-step reaction with 26 steps

1.1: LiAlH₄ / diethyl ether / 0 °C

2.1: imidazole / dimethylformamide / 0 °C

3.1: 4-methylmorpholine / CH₂Cl₂ / 20 °C

4.1: TBAF / tetrahydrofuran / 20 °C

5.1: 88 percent / SO₃*Py; DMSO; Et₃N / CH₂Cl₂ / 0 °C

6.1: 92 percent / SmI₂; MeOH / tetrahydrofuran / 0 °C

7.1: LiAlH₄ / diethyl ether / 0 °C

8.1: 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

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

10.1: 86 percent / pyridine / CH₂Cl₂ / 20 °C

11.1: dimethylsulfoxide / 50 °C

12.1: CH₂Cl₂ / Heating

13.1: DIBAL-H / CH₂Cl₂ / -78 °C

14.1: CH₂Cl₂ / Heating

15.1: 95 percent / DIBAL-H / CH₂Cl₂ / -78 °C

16.1: 90 percent / t-BuOOH; (+)-DET; 4 Angstroem MS / Ti(OiPr)4 / CH₂Cl₂ / -20 °C

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

18.1: NaHMDS / tetrahydrofuran / 0 °C

19.1: 92 percent / TBAF / tetrahydrofuran / 20 °C

20.1: 90 percent / PPTS / CH₂Cl₂ / 20 °C

21.1: KH / tetrahydrofuran / Heating

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

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

23.1: KH / tetrahydrofuran / Heating

24.1: CSA / methanol; CH₂Cl₂ / 0 - 20 °C

25.1: TEMPO; NaClO; KBr / CH₂Cl₂; H₂O / 0 °C

26.1: NaClO₂; 2-methyl-2-butene; NaH₂PO₄ / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 20 °C

With 4-methyl-morpholine; pyridine; 1H-imidazole; 2,6-dimethylpyridine; methanol; tert.-butylhydroperoxide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; samarium diiodide; 2-methyl-but-2-ene; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; 4 Angstroem MS; camphor-10-sulfonic acid; bis(cyclohexanyl)borane; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; potassium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; potassium bromide; titanium(IV) isopropylate; palladium hydroxide - carbon; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; 6.1: Nakata cyclization / 14.1: Wittig reaction / 16.1: Sharpless oxidation / 18.1: Wittig reaction;

DOI:10.1016/j.tetlet.2003.10.010

upstream raw materials:

((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

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

Downstream raw materials:

[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

{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