{(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

Base Information

• Chemical Name: {(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
• CAS No.: 602301-91-7
• Molecular Formula: C₄₃H₅₁NO₉
• Molecular Weight: 725.879
• Mol file: 602301-91-7.mol

Synonyms:{(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

Chemical Property of {(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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(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

There total 30 articles about {(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 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: 93.0%

sodium cyanide (143-33-9,25596-52-5) + 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 (602301-94-0) → {(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 (602301-91-7)

Guidance literature:

In dimethyl sulfoxide; at 50 ℃; for 18h;

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

Reference yield:

(E)-ethyl 4-((2R,4S,5R)-5-hydroxy-2-(4-methoxyphenyl)-1,3-dioxan-4-yl)but-2-enoate (602301-70-2) → {(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 (602301-91-7)

Guidance literature:

Multi-step reaction with 23 steps

1.1: imidazole / dimethylformamide

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

3.1: 139.35 g / diethyl-D-tartrate; molecular sieves 4 Angstroem; t-butylhydroperoxide / titanium(IV) tetraisopropoxide / CH₂Cl₂ / 27 h / -30 °C

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

5.1: 30 g / sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.33 h / 0 °C

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

7.1: 15.8 g / PPTS / CH₂Cl₂ / 3 h / 0 °C

8.1: 98 percent / imidazole / dimethylformamide / 1.5 h / 20 °C

9.1: 9-BBN dimer / tetrahydrofuran / 38 h / 20 °C

9.2: 83 percent / 10 percent NaOH; 30 percent H₂O₂ / 30 h / 20 °C

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

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

12.1: 9-BBN dimer / tetrahydrofuran / 96 h / 20 °C

12.2: 77 percent / 10 percent NaOH; 30 percent H₂O₂ / 30 h / 20 °C

13.1: 92 percent / n-Bu₃P; pyridine / 24 h

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

15.1: 86 percent / 2,6-di-t-butyl-4-methylpyridine; AgOTf; molecular sieves 4 Angstroem / CH₂Cl₂ / -75 - -30 °C

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

17.1: 395.4 mg / 4-methylmorpholine / CH₂Cl₂ / 1.5 h

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

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

18.3: NaBH₄ / methanol / 1 h

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

20.1: 61.7 mg / sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.17 h / 0 °C

21.1: PPTS / methanol / 1 h / 20 °C

21.2: 89 percent / PPTS / CH₂Cl₂; methanol / 1.5 h / 20 °C

22.1: 89 percent / molecular sieves 4 Angstroem / pyridine / 72 h

23.1: 93 percent / dimethylsulfoxide / 18 h / 50 °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; pyridine; methanol; tetrachloromethane; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; 3.1: Sharpless asymmetric epoxidation / 4.1: Swern oxidation / 5.1: Wittig reaction / 11.1: Wittig reaction / 20.1: Wittig reaction;

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

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,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 (602301-91-7)

Guidance literature:

Multi-step reaction with 22 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

20.1: PPTS / methanol / 1 h / 20 °C

20.2: 89 percent / PPTS / CH₂Cl₂; methanol / 1.5 h / 20 °C

21.1: 89 percent / molecular sieves 4 Angstroem / pyridine / 72 h

22.1: 93 percent / dimethylsulfoxide / 18 h / 50 °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; pyridine; methanol; tetrachloromethane; hexane; dichloromethane; dimethyl sulfoxide; 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

upstream raw materials:

sodium cyanide

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

p-Anisaldehyde dimethyl acetal

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

Downstream raw materials:

(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