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

Base Information

Chemical Name:(2aR*,3S*,5R*,5aR*,8S*,8aS*,8bS*)-methyl 3,5-<(S*)-benzylidenedioxy>-8-tert-butyldimethylsiloxyl-5a-formyl-4,5,5a,8,8a,8b-hexahydro-2H,3H-naphtho<1,8-bc>furan-2a-carboxylate
CAS No.:138175-81-2
Molecular Formula:C₂₇H₃₆O₇Si
Molecular Weight:500.664
Hs Code.:

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

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Suppliers and Price of (2aR*,3S*,5R*,5aR*,8S*,8aS*,8bS*)-methyl 3,5-<(S*)-benzylidenedioxy>-8-tert-butyldimethylsiloxyl-5a-formyl-4,5,5a,8,8a,8b-hexahydro-2H,3H-naphtho<1,8-bc>furan-2a-carboxylate

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Chemical Property of (2aR*,3S*,5R*,5aR*,8S*,8aS*,8bS*)-methyl 3,5-<(S*)-benzylidenedioxy>-8-tert-butyldimethylsiloxyl-5a-formyl-4,5,5a,8,8a,8b-hexahydro-2H,3H-naphtho<1,8-bc>furan-2a-carboxylate

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Technology Process of (2aR*,3S*,5R*,5aR*,8S*,8aS*,8bS*)-methyl 3,5-<(S*)-benzylidenedioxy>-8-tert-butyldimethylsiloxyl-5a-formyl-4,5,5a,8,8a,8b-hexahydro-2H,3H-naphtho<1,8-bc>furan-2a-carboxylate

There total 44 articles about (2aR*,3S*,5R*,5aR*,8S*,8aS*,8bS*)-methyl 3,5-<(S*)-benzylidenedioxy>-8-tert-butyldimethylsiloxyl-5a-formyl-4,5,5a,8,8a,8b-hexahydro-2H,3H-naphtho<1,8-bc>furan-2a-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: 85.0%

: C₃₄H₅₂O₇Si₂

: 138175-81-2,145840-57-9,145840-66-0
(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

Guidance literature:: With N-ethyl-1-[{4-(phenylazo)-phenyl}-azo]-2-naphthalenylamine; oxygen; ozone; triphenylphosphine; In dichloromethane; 1) -78 deg C, 1 h, 2) -78 deg C to room temperature, 12 h;
DOI:10.1039/P19920002735

Reference yield: 82.0%

: (2aR*,3S*,5R*,5aS*,8S*,8aS*,8bS*)-methyl 3,5-<(S*)-benzylidenedioxy>-8-tert-butyldimethylsiloxyl-5a-<(E,Z)-2-tert-butyldimethylsilyoxyvinyl>-4,5,5a,8,8a,8b-hexahydro-2H,3H-naphtho<1,8-bc>furan-2a-carboxylate

: 138175-81-2,145840-57-9,145840-66-0
(2aR*,3S*,5R*,5aR*,8S*,8aS*,8bS*)-methyl 3,5-<(S*)-benzylidenedioxy>-8-tert-butyldimethylsiloxyl-5a-formyl-4,5,5a,8,8a,8b-hexahydro-2H,3H-naphtho<1,8-bc>furan-2a-carboxylate

Guidance literature:: With N-ethyl-1-[{4-(phenylazo)-phenyl}-azo]-2-naphthalenylamine; oxygen; ozone; triphenylphosphine; In dichloromethane; 1) -78 deg C, 50 min, 2) -78 deg C to room temperature during 12 h;
DOI:10.1039/P19920002735

Reference yield:

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

: 138175-81-2,145840-57-9,145840-66-0
(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

Guidance literature:: Multi-step reaction with 10 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

With pyridine; peracetic acid; dmap; sodium tetrahydroborate; mercury(II) trifluoroacetate; pyridinium p-toluenesulfonate; potassium hydride; 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