(2aS,3R,5S,5aR,8S,8aR,8bR)-methyl 3,5-<(R)-benzylidenedioxy>-5a-(2'-pivaloyloxyethyl)-8-<(1''S,4''R)-4'',7'',7''-trimethyl-3''-oxo-2''-oxabicyclo<2.2.1>heptan-1''-ylcarbonyloxy>-4,5,5a,8,8a,8b-hexahydro-2H,3H-naphtho<1,8-bc>furan-2a-carboxylate

Base Information

Chemical Name:(2aS,3R,5S,5aR,8S,8aR,8bR)-methyl 3,5-<(R)-benzylidenedioxy>-5a-(2'-pivaloyloxyethyl)-8-<(1''S,4''R)-4'',7'',7''-trimethyl-3''-oxo-2''-oxabicyclo<2.2.1>heptan-1''-ylcarbonyloxy>-4,5,5a,8,8a,8b-hexahydro-2H,3H-naphtho<1,8-bc>furan-2a-carboxylate
CAS No.:145746-03-8
Molecular Formula:C₃₇H₄₆O₁₁
Molecular Weight:666.766
Hs Code.:

(2aS,3R,5S,5aR,8S,8aR,8bR)-methyl 3,5-<(R)-benzylidenedioxy>-5a-(2'-pivaloyloxyethyl)-8-<(1''S,4''R)-4'',7'',7''-trimethyl-3''-oxo-2''-oxabicyclo<2.2.1>heptan-1''-ylcarbonyloxy>-4,5,5a,8,8a,8b-hexahydro-2H,3H-naphtho<1,8-bc>furan-2a-carboxylate

Synonyms:

Suppliers and Price of (2aS,3R,5S,5aR,8S,8aR,8bR)-methyl 3,5-<(R)-benzylidenedioxy>-5a-(2'-pivaloyloxyethyl)-8-<(1''S,4''R)-4'',7'',7''-trimethyl-3''-oxo-2''-oxabicyclo<2.2.1>heptan-1''-ylcarbonyloxy>-4,5,5a,8,8a,8b-hexahydro-2H,3H-naphtho<1,8-bc>furan-2a-carboxylate

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Chemical Property of (2aS,3R,5S,5aR,8S,8aR,8bR)-methyl 3,5-<(R)-benzylidenedioxy>-5a-(2'-pivaloyloxyethyl)-8-<(1''S,4''R)-4'',7'',7''-trimethyl-3''-oxo-2''-oxabicyclo<2.2.1>heptan-1''-ylcarbonyloxy>-4,5,5a,8,8a,8b-hexahydro-2H,3H-naphtho<1,8-bc>furan-2a-carboxylate

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Technology Process of (2aS,3R,5S,5aR,8S,8aR,8bR)-methyl 3,5-<(R)-benzylidenedioxy>-5a-(2'-pivaloyloxyethyl)-8-<(1''S,4''R)-4'',7'',7''-trimethyl-3''-oxo-2''-oxabicyclo<2.2.1>heptan-1''-ylcarbonyloxy>-4,5,5a,8,8a,8b-hexahydro-2H,3H-naphtho<1,8-bc>furan-2a-carboxylate

There total 26 articles about (2aS,3R,5S,5aR,8S,8aR,8bR)-methyl 3,5-<(R)-benzylidenedioxy>-5a-(2'-pivaloyloxyethyl)-8-<(1''S,4''R)-4'',7'',7''-trimethyl-3''-oxo-2''-oxabicyclo<2.2.1>heptan-1''-ylcarbonyloxy>-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: 43.0%

: 39637-74-6
(1S)-(-)-camphanic chloride

: 145745-98-8,145840-55-7,145840-73-9,145840-74-0
(2aR*,3S*,5R*,5aS*,8R*,8aS*,8bS*)-methyl 3,5-<(S*)-benzylidenedioxy>-8-hydroxy-5a-(2'-pivaloyloxyethyl)-4,5,5a,8,8a,8b-hexahydro-2H,3H-naphtho<1,8-bc>furan-2a-carboxylate

: 145746-03-8,145840-61-5
(2aR,3S,5R,5aS,8R,8aS,8bS)-methyl 3,5-<(R)-benzylidenedioxy>-5a-(2'-pivaloyloxyethyl)-8-<(1''S,4''R)-4'',7'',7''-trimethyl-3''-oxo-2''-oxabicyclo<2.2.1>heptan-1''-ylcarbonyloxy>-4,5,5a,8,8a,8b-hexahydro-2H,3H-naphtho<1,8-bc>furan-2a-carboxylate

: 145746-03-8,145840-61-5
(2aS,3R,5S,5aR,8S,8aR,8bR)-methyl 3,5-<(R)-benzylidenedioxy>-5a-(2'-pivaloyloxyethyl)-8-<(1''S,4''R)-4'',7'',7''-trimethyl-3''-oxo-2''-oxabicyclo<2.2.1>heptan-1''-ylcarbonyloxy>-4,5,5a,8,8a,8b-hexahydro-2H,3H-naphtho<1,8-bc>furan-2a-carboxylate

Guidance literature:: With pyridine; dmap; In dichloromethane; for 21h; Ambient temperature;
DOI:10.1039/P19920002735

Reference yield: 43.0%

: 39637-74-6
(1S)-(-)-camphanic chloride

: 145745-98-8,145840-55-7,145840-73-9,145840-74-0
(2aR*,3S*,5R*,5aS*,8R*,8aS*,8bS*)-methyl 3,5-<(S*)-benzylidenedioxy>-8-hydroxy-5a-(2'-pivaloyloxyethyl)-4,5,5a,8,8a,8b-hexahydro-2H,3H-naphtho<1,8-bc>furan-2a-carboxylate

: 145746-03-8,145840-61-5
(2aR,3S,5R,5aS,8R,8aS,8bS)-methyl 3,5-<(R)-benzylidenedioxy>-5a-(2'-pivaloyloxyethyl)-8-<(1''S,4''R)-4'',7'',7''-trimethyl-3''-oxo-2''-oxabicyclo<2.2.1>heptan-1''-ylcarbonyloxy>-4,5,5a,8,8a,8b-hexahydro-2H,3H-naphtho<1,8-bc>furan-2a-carboxylate

: 145746-03-8,145840-61-5
(2aS,3R,5S,5aR,8S,8aR,8bR)-methyl 3,5-<(R)-benzylidenedioxy>-5a-(2'-pivaloyloxyethyl)-8-<(1''S,4''R)-4'',7'',7''-trimethyl-3''-oxo-2''-oxabicyclo<2.2.1>heptan-1''-ylcarbonyloxy>-4,5,5a,8,8a,8b-hexahydro-2H,3H-naphtho<1,8-bc>furan-2a-carboxylate

Guidance literature:: With pyridine; dmap; In dichloromethane; for 21h; Ambient temperature;
DOI:10.1039/P19920002735

Reference yield:

: 3282-30-2
pivaloyl chloride

: 145746-03-8,145840-61-5
(2aR,3S,5R,5aS,8R,8aS,8bS)-methyl 3,5-<(R)-benzylidenedioxy>-5a-(2'-pivaloyloxyethyl)-8-<(1''S,4''R)-4'',7'',7''-trimethyl-3''-oxo-2''-oxabicyclo<2.2.1>heptan-1''-ylcarbonyloxy>-4,5,5a,8,8a,8b-hexahydro-2H,3H-naphtho<1,8-bc>furan-2a-carboxylate

Guidance literature:: Multi-step reaction with 9 steps

1: 81 percent / pyridine, DMAP / CH₂Cl₂ / 72 h / 45 °C

2: 14 percent / NaBH₄ / methanol; tetrahydrofuran / 1.5 h

3: 79 percent / triethylamine / CH₂Cl₂; acetonitrile / 0.75 h / 0 °C

4: 100 percent / methyl iodide, CaCO₃, water / acetonitrile / 7 h / 55 °C

5: 100 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / CH₂Cl₂ / 2.25 h / Ambient temperature

6: 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

7: 83 percent / pyridinium tosate / benzene / 24.5 h

8: 97 percent / L-selectride / tetrahydrofuran / 0.25 h / -78 °C

9: 44 percent / DMAP, pyridine / CH₂Cl₂ / 21 h / Ambient temperature

With pyridine; peracetic acid; dmap; sodium tetrahydroborate; water; mercury(II) trifluoroacetate; pyridinium p-toluenesulfonate; L-Selectride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic acid; calcium carbonate; methyl iodide; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; benzene;
DOI:10.1039/P19920002735