(2R,4aR,5aS,8R,9S,10aR,11aS)-9-Allyl-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]naphthalene

Base Information

• Chemical Name: (2R,4aR,5aS,8R,9S,10aR,11aS)-9-Allyl-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]naphthalene
• CAS No.: 602301-88-2
• Molecular Formula: C₄₆H₆₀O₁₁
• Molecular Weight: 788.976

Synonyms:(2R,4aR,5aS,8R,9S,10aR,11aS)-9-Allyl-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]naphthalene

Chemical Property of (2R,4aR,5aS,8R,9S,10aR,11aS)-9-Allyl-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]naphthalene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4aR,5aS,8R,9S,10aR,11aS)-9-Allyl-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]naphthalene

There total 26 articles about (2R,4aR,5aS,8R,9S,10aR,11aS)-9-Allyl-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]naphthalene 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)-4-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-but-2-enoic acid ethyl ester (602301-71-3) → (2R,4aR,5aS,8R,9S,10aR,11aS)-9-Allyl-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]naphthalene (602301-88-2)

Guidance literature:

Multi-step reaction with 19 steps

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

2.1: 139.35 g / diethyl-D-tartrate; molecular sieves 4 Angstroem; t-butylhydroperoxide / titanium(IV) tetraisopropoxide / CH₂Cl₂ / 27 h / -30 °C

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

4.1: 30 g / sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.33 h / 0 °C

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

6.1: 15.8 g / PPTS / CH₂Cl₂ / 3 h / 0 °C

7.1: 98 percent / imidazole / dimethylformamide / 1.5 h / 20 °C

8.1: 9-BBN dimer / tetrahydrofuran / 38 h / 20 °C

8.2: 83 percent / 10 percent NaOH; 30 percent H₂O₂ / 30 h / 20 °C

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

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

11.1: 9-BBN dimer / tetrahydrofuran / 96 h / 20 °C

11.2: 77 percent / 10 percent NaOH; 30 percent H₂O₂ / 30 h / 20 °C

12.1: 92 percent / n-Bu₃P; pyridine / 24 h

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

14.1: 86 percent / 2,6-di-t-butyl-4-methylpyridine; AgOTf; molecular sieves 4 Angstroem / CH₂Cl₂ / -75 - -30 °C

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

16.1: 395.4 mg / 4-methylmorpholine / CH₂Cl₂ / 1.5 h

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

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

17.3: NaBH₄ / methanol / 1 h

18.1: DMSO; Et₃N; SO₃*pyridine / CH₂Cl₂ / 2 h

19.1: 61.7 mg / sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.17 h / 0 °C

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; 2.1: Sharpless asymmetric epoxidation / 3.1: Swern oxidation / 4.1: Wittig reaction / 10.1: Wittig reaction / 19.1: Wittig reaction;

DOI:10.1016/S0040-4020(03)00913-X

Reference yield:

p-Anisaldehyde dimethyl acetal (2186-92-7) → (2R,4aR,5aS,8R,9S,10aR,11aS)-9-Allyl-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]naphthalene (602301-88-2)

Guidance literature:

Multi-step reaction with 21 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

20.1: DMSO; Et₃N; SO₃*pyridine / CH₂Cl₂ / 2 h

21.1: 61.7 mg / sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.17 h / 0 °C

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 / 21.1: Wittig reaction;

DOI:10.1016/S0040-4020(03)00913-X

Reference yield:

Methyltriphenylphosphonium bromide (1779-49-3) + [(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]-acetaldehyde → (2R,4aR,5aS,8R,9S,10aR,11aS)-9-Allyl-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]naphthalene (602301-88-2)

Guidance literature:

With sodium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃; for 0.166667h;

DOI:10.1016/S0040-4020(03)00913-X

upstream raw materials:

Methyltriphenylphosphonium bromide

p-Anisaldehyde dimethyl acetal

(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-(1-ethoxy-ethoxymethyl)-tetrahydro-pyran-3-ol

tert-Butyl-[(2R,4aR,6S,7R,8aS)-2-(4-methoxy-phenyl)-6-(3-phenylsulfanyl-propyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy]-dimethyl-silane

Downstream raw materials:

(2R,4aR,5aS,8R,9S,10aR,11aS)-9-Allyl-8-((2R,3S,5R,6S)-5-benzyloxy-6-benzyloxymethyl-2-vinyl-tetrahydro-pyran-3-yloxy)-2-(4-methoxy-phenyl)-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene

{(2R,3S,5R,6S)-3-[(2R,4aR,5aS,8R,9S,10aR,11aS)-9-Allyl-2-(4-methoxy-phenyl)-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-8-yloxy]-5-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl}-acetonitrile

(2R,4aR,5aS,8R,9S,10aR,11aS)-9-Allyl-8-((2R,3S,5R,6S)-2-allyl-5-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-2-(4-methoxy-phenyl)-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene

Toluene-4-sulfonic acid (2R,3S,5R,6S)-3-[(2R,4aR,5aS,8R,9S,10aR,11aS)-9-allyl-2-(4-methoxy-phenyl)-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-8-yloxy]-5-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl ester

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