2-[(2R,4aR,5aS,8R,9S,10aR,11aS)-8-[(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-(1-ethoxy-ethoxymethyl)-tetrahydro-pyran-3-yloxy]-2-(4-methoxy-phenyl)-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-9-yl]-ethanol

Base Information

Chemical Name:2-[(2R,4aR,5aS,8R,9S,10aR,11aS)-8-[(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-(1-ethoxy-ethoxymethyl)-tetrahydro-pyran-3-yloxy]-2-(4-methoxy-phenyl)-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-9-yl]-ethanol
CAS No.:602301-82-6
Molecular Formula:C₄₅H₆₀O₁₂
Molecular Weight:792.964
Hs Code.:

2-[(2R,4aR,5aS,8R,9S,10aR,11aS)-8-[(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-(1-ethoxy-ethoxymethyl)-tetrahydro-pyran-3-yloxy]-2-(4-methoxy-phenyl)-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-9-yl]-ethanol

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Chemical Property of 2-[(2R,4aR,5aS,8R,9S,10aR,11aS)-8-[(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-(1-ethoxy-ethoxymethyl)-tetrahydro-pyran-3-yloxy]-2-(4-methoxy-phenyl)-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-9-yl]-ethanol

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Technology Process of 2-[(2R,4aR,5aS,8R,9S,10aR,11aS)-8-[(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-(1-ethoxy-ethoxymethyl)-tetrahydro-pyran-3-yloxy]-2-(4-methoxy-phenyl)-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-9-yl]-ethanol

There total 23 articles about 2-[(2R,4aR,5aS,8R,9S,10aR,11aS)-8-[(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-(1-ethoxy-ethoxymethyl)-tetrahydro-pyran-3-yloxy]-2-(4-methoxy-phenyl)-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-9-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:

: (E)-3-[(2R,4aR,6S,7S,8aS)-6-{3-[(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-(1-ethoxy-ethoxymethyl)-tetrahydro-pyran-3-yloxy]-3-phenylsulfanyl-propyl}-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acrylic acid methyl ester

: 602301-82-6
2-[(2R,4aR,5aS,8R,9S,10aR,11aS)-8-[(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-(1-ethoxy-ethoxymethyl)-tetrahydro-pyran-3-yloxy]-2-(4-methoxy-phenyl)-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-9-yl]-ethanol

Guidance literature:: (E)-3-[(2R,4aR,6S,7S,8aS)-6-{3-[(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-(1-ethoxy-ethoxymethyl)-tetrahydro-pyran-3-yloxy]-3-phenylsulfanyl-propyl}-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acrylic acid methyl ester; With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 80 ℃; for 9h;

With diisobutylaluminium hydride; In dichloromethane; toluene; at -78 ℃; for 0.5h;

With sodium tetrahydroborate; In methanol; for 1h;
DOI:10.1016/S0040-4020(03)00913-X

Reference yield:

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 602301-82-6
2-[(2R,4aR,5aS,8R,9S,10aR,11aS)-8-[(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-(1-ethoxy-ethoxymethyl)-tetrahydro-pyran-3-yloxy]-2-(4-methoxy-phenyl)-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-9-yl]-ethanol

Guidance literature:: Multi-step reaction with 19 steps

1.1: tetrahydrofuran / Heating

1.2: 82 percent / CSA / CH₂Cl₂; tetrahydrofuran / 24 h / 20 °C

2.1: imidazole / dimethylformamide

3.1: DIBAL / CH₂Cl₂; hexane / 1 h / -78 °C

4.1: 139.35 g / diethyl-D-tartrate; molecular sieves 4 Angstroem; t-butylhydroperoxide / titanium(IV) tetraisopropoxide / CH₂Cl₂ / 27 h / -30 °C

5.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 °C

6.1: 30 g / sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.33 h / 0 °C

7.1: TBAF / tetrahydrofuran / 0.5 h / 20 °C

8.1: 15.8 g / PPTS / CH₂Cl₂ / 3 h / 0 °C

9.1: 98 percent / imidazole / dimethylformamide / 1.5 h / 20 °C

10.1: 9-BBN dimer / tetrahydrofuran / 38 h / 20 °C

10.2: 83 percent / 10 percent NaOH; 30 percent H₂O₂ / 30 h / 20 °C

11.1: DMSO; Et₃N; SO₃*pyridine / CH₂Cl₂ / 3 h / 20 °C

12.1: t-BuOK / tetrahydrofuran / 1.5 h / 20 °C

13.1: 9-BBN dimer / tetrahydrofuran / 96 h / 20 °C

13.2: 77 percent / 10 percent NaOH; 30 percent H₂O₂ / 30 h / 20 °C

14.1: 92 percent / n-Bu₃P; pyridine / 24 h

15.1: N-chlorosuccinimide / CCl₄ / 0.33 h / 20 °C

16.1: 86 percent / 2,6-di-t-butyl-4-methylpyridine; AgOTf; molecular sieves 4 Angstroem / CH₂Cl₂ / -75 - -30 °C

17.1: TBAF / tetrahydrofuran / 12 h / 20 °C

18.1: 395.4 mg / 4-methylmorpholine / CH₂Cl₂ / 1.5 h

19.1: n-Bu₃SnH; AIBN / toluene / 9 h / 80 °C

19.2: DIBAL / CH₂Cl₂; toluene / 0.5 h / -78 °C

19.3: NaBH₄ / methanol / 1 h

With 4-methyl-morpholine; pyridine; 1H-imidazole; tert.-butylhydroperoxide; N-chloro-succinimide; 2,6-di-tert-butyl-4-methylpyridine; oxalyl dichloride; pyridine-SO₃ complex; 2,2'-azobis(isobutyronitrile); diethyl (2S,3S)-tartrate; tributylphosphine; 4 A molecular sieve; potassium tert-butylate; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; silver trifluoromethanesulfonate; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; dimeric 9-borabicyclo[3.3.1]nonane; titanium(IV) isopropylate; In tetrahydrofuran; tetrachloromethane; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: Wittig reaction / 4.1: Sharpless asymmetric epoxidation / 5.1: Swern oxidation / 6.1: Wittig reaction / 12.1: Wittig reaction;
DOI:10.1016/S0040-4020(03)00913-X

Reference yield:

: 602301-65-5
(2R,4aR,6S,7R,8aS)-2-(4-Methoxy-phenyl)-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

: 602301-82-6
2-[(2R,4aR,5aS,8R,9S,10aR,11aS)-8-[(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-(1-ethoxy-ethoxymethyl)-tetrahydro-pyran-3-yloxy]-2-(4-methoxy-phenyl)-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-9-yl]-ethanol

Guidance literature:: Multi-step reaction with 11 steps

1.1: 98 percent / imidazole / dimethylformamide / 1.5 h / 20 °C

2.1: 9-BBN dimer / tetrahydrofuran / 38 h / 20 °C

2.2: 83 percent / 10 percent NaOH; 30 percent H₂O₂ / 30 h / 20 °C

3.1: DMSO; Et₃N; SO₃*pyridine / CH₂Cl₂ / 3 h / 20 °C

4.1: t-BuOK / tetrahydrofuran / 1.5 h / 20 °C

5.1: 9-BBN dimer / tetrahydrofuran / 96 h / 20 °C

5.2: 77 percent / 10 percent NaOH; 30 percent H₂O₂ / 30 h / 20 °C

6.1: 92 percent / n-Bu₃P; pyridine / 24 h

7.1: N-chlorosuccinimide / CCl₄ / 0.33 h / 20 °C

8.1: 86 percent / 2,6-di-t-butyl-4-methylpyridine; AgOTf; molecular sieves 4 Angstroem / CH₂Cl₂ / -75 - -30 °C

9.1: TBAF / tetrahydrofuran / 12 h / 20 °C

10.1: 395.4 mg / 4-methylmorpholine / CH₂Cl₂ / 1.5 h

11.1: n-Bu₃SnH; AIBN / toluene / 9 h / 80 °C

11.2: DIBAL / CH₂Cl₂; toluene / 0.5 h / -78 °C

11.3: NaBH₄ / methanol / 1 h

With 4-methyl-morpholine; pyridine; 1H-imidazole; N-chloro-succinimide; 2,6-di-tert-butyl-4-methylpyridine; pyridine-SO₃ complex; 2,2'-azobis(isobutyronitrile); tributylphosphine; 4 A molecular sieve; potassium tert-butylate; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; silver trifluoromethanesulfonate; dimethyl sulfoxide; triethylamine; dimeric 9-borabicyclo[3.3.1]nonane; In tetrahydrofuran; tetrachloromethane; dichloromethane; N,N-dimethyl-formamide; toluene; 4.1: Wittig reaction;
DOI:10.1016/S0040-4020(03)00913-X