(2aR,4aS,5SR,7aS,8S,10R,10aS,10bR)-dimethyl 8,9-<(R)benzylidenedioxy>-5-hydroxy-3-oxoperhydronaphtho<1,8-bc:4,4a-c'>difuran-5,10a-dicarboxylate

Base Information

• Chemical Name: (2aR,4aS,5SR,7aS,8S,10R,10aS,10bR)-dimethyl 8,9-<(R)benzylidenedioxy>-5-hydroxy-3-oxoperhydronaphtho<1,8-bc:4,4a-c'>difuran-5,10a-dicarboxylate
• CAS No.: 145746-05-0
• Molecular Formula: C₂₄H₂₆O₁₀
• Molecular Weight: 474.464

Synonyms:

Chemical Property of (2aR,4aS,5SR,7aS,8S,10R,10aS,10bR)-dimethyl 8,9-<(R)benzylidenedioxy>-5-hydroxy-3-oxoperhydronaphtho<1,8-bc:4,4a-c'>difuran-5,10a-dicarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2aR,4aS,5SR,7aS,8S,10R,10aS,10bR)-dimethyl 8,9-<(R)benzylidenedioxy>-5-hydroxy-3-oxoperhydronaphtho<1,8-bc:4,4a-c'>difuran-5,10a-dicarboxylate

There total 25 articles about (2aR,4aS,5SR,7aS,8S,10R,10aS,10bR)-dimethyl 8,9-<(R)benzylidenedioxy>-5-hydroxy-3-oxoperhydronaphtho<1,8-bc:4,4a-c'>difuran-5,10a-dicarboxylate 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: 74.0%

benzaldehyde (100-52-7) + (2aR,4aS,5SR,7aS,8S,10R,10aS,10bR)-dimethyl 5,8,10-trihydroxy-3-oxoperhydronaphtho<1,8-bc:4,4a-c'>difuran-5,10a-dicarboxylate (138175-69-6,145840-60-4,145840-79-5) → (2aR,4aS,5SR,7aS,8S,10R,10aS,10bR)-dimethyl 8,9-<(R)benzylidenedioxy>-5-hydroxy-3-oxoperhydronaphtho<1,8-bc:4,4a-c'>difuran-5,10a-dicarboxylate (145746-05-0,145840-80-8)

Guidance literature:

With pyridinium p-toluenesulfonate; In benzene; for 4.5h;

DOI:10.1039/P19920002735

Reference yield:

(2aR*,3R*,4aR*,7aS*,8S*,10aR*,10bR*)-methyl 3-dimethyl(phenyl)silyl-8-hydroxy-4a-methoxyperhydronaphtho<1,8-bc:5,4a-b'>difuran-10-spiro-2'-(1',3'-dithiane)-2a-carboxylate (145745-84-2) → (2aR,4aS,5SR,7aS,8S,10R,10aS,10bR)-dimethyl 8,9-<(R)benzylidenedioxy>-5-hydroxy-3-oxoperhydronaphtho<1,8-bc:4,4a-c'>difuran-5,10a-dicarboxylate (145746-05-0,145840-80-8)

Guidance literature:

Multi-step reaction with 24 steps

1: 59 percent / toluene-p-sulfonic acid monohydrate / acetonitrile; H₂O / 4.75 h / 1) 53 deg C, 4.75 h, 2) room temperature, 1.5 h

2: 81 percent / pyridine, DMAP / CH₂Cl₂ / 72 h / 45 °C

3: 14 percent / NaBH₄ / methanol; tetrahydrofuran / 1.5 h

4: 79 percent / triethylamine / CH₂Cl₂; acetonitrile / 0.75 h / 0 °C

5: 100 percent / methyl iodide, CaCO₃, water / acetonitrile / 7 h / 55 °C

6: 100 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / CH₂Cl₂ / 2.25 h / Ambient temperature

7: 1) glacial acetic acid, trifluoroacetic acid, mercury(II) trifluoroacetate, 2) 32 wtpercent peracetic acid / 1) room temperature, 10 min, 2a) 10 deg C, 5 min, b) room temperature, 2 h

8: 83 percent / pyridinium tosate / benzene / 24.5 h

9: 97 percent / L-selectride / tetrahydrofuran / 0.25 h / -78 °C

10: 44 percent / DMAP, pyridine / CH₂Cl₂ / 21 h / Ambient temperature

11: 1) potassium carbonate, 2) pyridine / 1) methanol, room temperature, 11 h, 2) methylene chloride, 45 min

12: 96 percent / 2,6-lutidine / CH₂Cl₂ / 0.42 h / 0 °C

13: LiOH*H₂O / ethanol; H₂O / 5 h / 60 °C

14: 90 percent / Dess-Martin triacetoxyperiodinane reagent, pyridine / CH₂Cl₂ / 0.42 h / Ambient temperature

15: triethylamine / CH₂Cl₂ / 2.5 h / -15 - 5 °C

16: 85 percent / 1) O₂/O₃, Sudan Red 7B, 2) triphenylphosphine / CH₂Cl₂ / 1) -78 deg C, 1 h, 2) -78 deg C to room temperature, 12 h

17: zinc borohydride / diethyl ether; tetrahydrofuran / 3 h / -10 °C

18: toluene-p-sulfonyl chloride / CH₂Cl₂ / 0.33 h / Ambient temperature

19: 93 percent / tetrabutylammonium fluoride, powdered activated 4 Angstroem molecular sieves / tetrahydrofuran / 4 h / Ambient temperature

20: 88 percent / pyridinium dichromate, powdered activated 4 Angstroem molekular sieves / CH₂Cl₂ / 2.75 h / Ambient temperature

21: 100 percent / lithium hexamethyldisilazide / tetrahydrofuran / O deg C to room temperature, 70 min

22: dimethyldioxirane / acetone / 0.37 h / 0 °C

23: pyridinium tosate / methanol / 5.5 h

24: 74 percent / pyridinium tosate / benzene / 4.5 h

With pyridine; 2,6-dimethylpyridine; peracetic acid; dmap; lithium hydroxide; sodium tetrahydroborate; dipyridinium dichromate; 4 A molecular sieve; zinc borohydride; N-ethyl-1-[{4-(phenylazo)-phenyl}-azo]-2-naphthalenylamine; tetrabutyl ammonium fluoride; water; oxygen; mercury(II) trifluoroacetate; 3,3-dimethyldioxirane; pyridinium p-toluenesulfonate; L-Selectride; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; ozone; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; p-toluenesulfonyl chloride; triphenylphosphine; trifluoroacetic acid; calcium carbonate; lithium hexamethyldisilazane; methyl iodide; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; acetone; acetonitrile; benzene;

DOI:10.1039/P19920002735

Reference yield:

(2aR*,3R*,5aS*,6S*,8aR*,8bR*)-methyl 3-dimethyl(phenyl)silyl-5-oxo-6-pivaloyloxy-5a-(2''-pivaloyloxyethyl)perhydronaphtho<1,8-bc>furan-8-spiro-2'-(1',3'-dithiane)-2a-carboxylate (138175-75-4) → (2aR,4aS,5SR,7aS,8S,10R,10aS,10bR)-dimethyl 8,9-<(R)benzylidenedioxy>-5-hydroxy-3-oxoperhydronaphtho<1,8-bc:4,4a-c'>difuran-5,10a-dicarboxylate (145746-05-0,145840-80-8)

Guidance literature:

Multi-step reaction with 22 steps

1: 14 percent / NaBH₄ / methanol; tetrahydrofuran / 1.5 h

2: 79 percent / triethylamine / CH₂Cl₂; acetonitrile / 0.75 h / 0 °C

3: 100 percent / methyl iodide, CaCO₃, water / acetonitrile / 7 h / 55 °C

4: 100 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / CH₂Cl₂ / 2.25 h / Ambient temperature

5: 1) glacial acetic acid, trifluoroacetic acid, mercury(II) trifluoroacetate, 2) 32 wtpercent peracetic acid / 1) room temperature, 10 min, 2a) 10 deg C, 5 min, b) room temperature, 2 h

6: 83 percent / pyridinium tosate / benzene / 24.5 h

7: 97 percent / L-selectride / tetrahydrofuran / 0.25 h / -78 °C

8: 44 percent / DMAP, pyridine / CH₂Cl₂ / 21 h / Ambient temperature

9: 1) potassium carbonate, 2) pyridine / 1) methanol, room temperature, 11 h, 2) methylene chloride, 45 min

10: 96 percent / 2,6-lutidine / CH₂Cl₂ / 0.42 h / 0 °C

11: LiOH*H₂O / ethanol; H₂O / 5 h / 60 °C

12: 90 percent / Dess-Martin triacetoxyperiodinane reagent, pyridine / CH₂Cl₂ / 0.42 h / Ambient temperature

13: triethylamine / CH₂Cl₂ / 2.5 h / -15 - 5 °C

14: 85 percent / 1) O₂/O₃, Sudan Red 7B, 2) triphenylphosphine / CH₂Cl₂ / 1) -78 deg C, 1 h, 2) -78 deg C to room temperature, 12 h

15: zinc borohydride / diethyl ether; tetrahydrofuran / 3 h / -10 °C

16: toluene-p-sulfonyl chloride / CH₂Cl₂ / 0.33 h / Ambient temperature

17: 93 percent / tetrabutylammonium fluoride, powdered activated 4 Angstroem molecular sieves / tetrahydrofuran / 4 h / Ambient temperature

18: 88 percent / pyridinium dichromate, powdered activated 4 Angstroem molekular sieves / CH₂Cl₂ / 2.75 h / Ambient temperature

19: 100 percent / lithium hexamethyldisilazide / tetrahydrofuran / O deg C to room temperature, 70 min

20: dimethyldioxirane / acetone / 0.37 h / 0 °C

21: pyridinium tosate / methanol / 5.5 h

22: 74 percent / pyridinium tosate / benzene / 4.5 h

With pyridine; 2,6-dimethylpyridine; peracetic acid; dmap; lithium hydroxide; sodium tetrahydroborate; dipyridinium dichromate; 4 A molecular sieve; zinc borohydride; N-ethyl-1-[{4-(phenylazo)-phenyl}-azo]-2-naphthalenylamine; tetrabutyl ammonium fluoride; water; oxygen; mercury(II) trifluoroacetate; 3,3-dimethyldioxirane; pyridinium p-toluenesulfonate; L-Selectride; potassium carbonate; Dess-Martin periodane; ozone; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; p-toluenesulfonyl chloride; triphenylphosphine; trifluoroacetic acid; calcium carbonate; lithium hexamethyldisilazane; methyl iodide; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; acetone; acetonitrile; benzene;

DOI:10.1039/P19920002735

upstream raw materials:

benzaldehyde

(2aR,4aS,5SR,7aS,8S,10R,10aS,10bR)-dimethyl 5,8,10-trihydroxy-3-oxoperhydronaphtho<1,8-bc:4,4a-c'>difuran-5,10a-dicarboxylate

(2aR,4aR,5RS,8aR,9S,11R,11aS,11bS)-methyl 9,11-<(R)-benzylidenedioxy>-5-cyano3,6-dioxoperhydrofuro<2',3',4';4,5>naphtho<8a,1-c>pyran-11a-carboxylate

(2aS,3R,5S,5aS,8S,8aR,8bR)-methyl 3,5-<(R)-benzylidenedioxy>-8-tert-butyldimethylsiloxy-5a-formyl-4,5,5a,8,8a,8b-hexahydro-2H,3H-naphtho<1,8-bc>furan-2a-carboxylate

Downstream raw materials:

(2aR,4aS,5R,7aS,8S,10R,10aS,10bR)-dimethyl 8,9-<(R)benzylidenedioxy>-5-benzyloxy-3-oxoperhydronaphtho<1,8-bc:4,4a-c'>difuran-5,10a-dicarboxylate

<2aR, 4aS, 5S, 7aS, 8S, 10R, 10aS, 10bR> dimethyl 5-benzyloxy-3-oxo-8,10-phenylmethylenedioxyperhydronaphto<1,8-bc:4,4a-c'>difuran-5,10a-dicarboxylate

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