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

Base Information

Chemical Name:(2aR*,4aR*,5RS,8aR*,9S*,11R*,11aS*,11bS*)-methyl 9,11-<(R*)-benzylidenedioxy>-5-cyano-3,6-dioxoperhydrofuro<2',3',4';4,5>-naphtho<8a,1-c>pyran-11a-carboxylate
CAS No.:138175-83-4
Molecular Formula:C₂₄H₂₃NO₈
Molecular Weight:453.449
Hs Code.:

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

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

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

There total 54 articles about (2aR*,4aR*,5RS,8aR*,9S*,11R*,11aS*,11bS*)-methyl 9,11-<(R*)-benzylidenedioxy>-5-cyano-3,6-dioxoperhydrofuro<2',3',4';4,5>-naphtho<8a,1-c>pyran-11a-carboxylate 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: 100.0%

: 145746-02-7,145840-77-3
(2aS,3R,5S,5aR,8aR,8bR)-methyl 3,5-<(R)-benzylidenedioxy>-5a-cyanoacetoxymethyl-8-oxo-4,5,5a,8,8a,8b-hexahydro-2H,3H-naphtho<1,8-bc>furan-2a-carboxylate

: 138175-83-4,145840-59-1,145840-78-4,145840-81-9,145840-82-0
(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

Guidance literature:: With lithium hexamethyldisilazane; In tetrahydrofuran; O deg C to room temperature, 70 min;
DOI:10.1039/P19920002735

Reference yield: 100.0%

: 145746-02-7,145840-77-3
(2aR*,3S*,5R*,5aS*,8aS*,8bS*)-methyl 3,5-<(S*)-benzylidenedioxy>-5a-cyanoacetoxymethyl-8-oxo-4,5,5a,8,8a,8b-hexahydro-2H,3H-naphtho<1,8-bc>furan-2a-carboxylate

: 138175-83-4,145840-59-1,145840-78-4,145840-81-9,145840-82-0
(2aR*,4aR*,5RS,8aR*,9S*,11R*,11aS*,11bS*)-methyl 9,11-<(R*)-benzylidenedioxy>-5-cyano-3,6-dioxoperhydrofuro<2',3',4';4,5>-naphtho<8a,1-c>pyran-11a-carboxylate

Guidance literature:: With lithium hexamethyldisilazane; In tetrahydrofuran; hexane; 0 deg C to room temperature, 70 min;
DOI:10.1039/P19920002735

Reference yield:

: 145745-77-3
(Z)-methyl 2-bromomethyl-3-dimethyl(phenyl)silylprop-2-enoate

: 138175-83-4,145840-59-1,145840-78-4,145840-81-9,145840-82-0
(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

Guidance literature:: Multi-step reaction with 12 steps

1: 60 percent / KH

3: pTSA / H₂O; acetonitrile / 5.5 h / 55 °C

4: 89 percent / pyridine, DMAP / 45 °C

5: 96 percent / NaBH₄ / tetrahydrofuran; methanol

6: 1) MeI / 2) DBU / 1) CH₃CN, reflux

7: 1) Hg(O₂CCF₃)2, 2) CH₃CO₃H / 1) TFA, AcOH, 10 min

8: 94 percent / PPTS / benzene / Heating

11: 1) Zn(BH₄)2, 2) pTosCl, pyridine / 1) -10 deg C

With pyridine; peracetic acid; dmap; sodium tetrahydroborate; zinc(II) tetrahydroborate; mercury(II) trifluoroacetate; pyridinium p-toluenesulfonate; potassium hydride; p-toluenesulfonyl chloride; methyl iodide; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; water; acetonitrile; benzene;
DOI:10.1016/0040-4039(91)80785-5