methyl (2S,3R,3aS,5'R,6S,7aR)-3-<(benzyloxy)methoxy>-3-<(benzyloxy)methyl>decahydro-5'-methyl-4'-oxospiropyran>-6-carboxylate

Base Information

Chemical Name:methyl (2S,3R,3aS,5'R,6S,7aR)-3-<(benzyloxy)methoxy>-3-<(benzyloxy)methyl>decahydro-5'-methyl-4'-oxospiropyran>-6-carboxylate
CAS No.:88671-06-1
Molecular Formula:C₃₁H₃₈O₈
Molecular Weight:538.638
Hs Code.:

methyl (2S,3R,3aS,5'R,6S,7aR)-3-<(benzyloxy)methoxy>-3-<(benzyloxy)methyl>decahydro-5'-methyl-4'-oxospiro<benzofuran-2(3H),2'-<2H>pyran>-6-carboxylate

Synonyms:methyl (2S,3R,3aS,5'R,6S,7aR)-3-<(benzyloxy)methoxy>-3-<(benzyloxy)methyl>decahydro-5'-methyl-4'-oxospiropyran>-6-carboxylate

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Chemical Property of methyl (2S,3R,3aS,5'R,6S,7aR)-3-<(benzyloxy)methoxy>-3-<(benzyloxy)methyl>decahydro-5'-methyl-4'-oxospiropyran>-6-carboxylate

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Technology Process of methyl (2S,3R,3aS,5'R,6S,7aR)-3-<(benzyloxy)methoxy>-3-<(benzyloxy)methyl>decahydro-5'-methyl-4'-oxospiropyran>-6-carboxylate

There total 11 articles about methyl (2S,3R,3aS,5'R,6S,7aR)-3-<(benzyloxy)methoxy>-3-<(benzyloxy)methyl>decahydro-5'-methyl-4'-oxospiropyran>-6-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:

: 88670-93-3
(1S,2S,4S)-7-<(benzyloxy)methoxy>-2,9-dihydroxy-p-methane-7-carbonitrile

: 88671-06-1
methyl (2S,3R,3aS,5'R,6S,7aR)-3-<(benzyloxy)methoxy>-3-<(benzyloxy)methyl>decahydro-5'-methyl-4'-oxospiropyran>-6-carboxylate

Guidance literature:: Multi-step reaction with 8 steps

1: 40percent aqueous KOH / ethanol / 2 h / 120 °C

2: triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / -20 °C

3: Jones reagent / acetone / 0.5 h / 0 °C

4: 1.) cupric acetate monohydrate 2.) lead tetraacetate / pyridine / 1.) 0.5 h, room temperature 2a.) 1 h, 23 deg C 2b.) 2 h, 80 deg C

5: LDA / 1.) -78 deg C, 1 h 2.) -40 deg C, 2 h

6: anhydrous zinc chloride

7: 1.) ozone 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C 2.) 23 deg, 26 h

8: 1.) Jones reagent 2.) CH₂N₂ / 1a.) acetone, -10 deg C, 20 min 1b.) -5 deg C

With diazomethane; lead(IV) acetate; potassium hydroxide; jones reagent; dimethylsulfide; copper diacetate; ozone; triphenylphosphine; zinc(II) chloride; lithium diisopropyl amide; diethylazodicarboxylate; pyridine; In tetrahydrofuran; ethanol; acetone;
DOI:10.1021/jo00179a018

Reference yield:

: 82167-73-5
(4S)-7-<(benzyloxy)methoxy>-p-mentha-1,8-diene-7-carbonitrile

: 88671-06-1
methyl (2S,3R,3aS,5'R,6S,7aR)-3-<(benzyloxy)methoxy>-3-<(benzyloxy)methyl>decahydro-5'-methyl-4'-oxospiropyran>-6-carboxylate

Guidance literature:: Multi-step reaction with 9 steps

1: 1.) thexylborane 2.) 30percent H₂O₂, NaOAc / 1.a.) -40 deg C 1.b.) 3 h, 23 deg C 2.) 1 h, 50 deg C

2: 40percent aqueous KOH / ethanol / 2 h / 120 °C

3: triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / -20 °C

4: Jones reagent / acetone / 0.5 h / 0 °C

5: 1.) cupric acetate monohydrate 2.) lead tetraacetate / pyridine / 1.) 0.5 h, room temperature 2a.) 1 h, 23 deg C 2b.) 2 h, 80 deg C

6: LDA / 1.) -78 deg C, 1 h 2.) -40 deg C, 2 h

7: anhydrous zinc chloride

8: 1.) ozone 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C 2.) 23 deg, 26 h

9: 1.) Jones reagent 2.) CH₂N₂ / 1a.) acetone, -10 deg C, 20 min 1b.) -5 deg C

With diazomethane; lead(IV) acetate; potassium hydroxide; jones reagent; dimethylsulfide; thexylborane; dihydrogen peroxide; copper diacetate; sodium acetate; ozone; triphenylphosphine; zinc(II) chloride; lithium diisopropyl amide; diethylazodicarboxylate; pyridine; In tetrahydrofuran; ethanol; acetone;
DOI:10.1021/jo00179a018

Reference yield:

: 82167-75-7
(3aS,6S,7aR)-3-<(benzyloxy)methoxy>hexahydro-6-(2-hydroxy-1-methylethyl)-2(3H)-benzofuranone

: 88671-06-1
methyl (2S,3R,3aS,5'R,6S,7aR)-3-<(benzyloxy)methoxy>-3-<(benzyloxy)methyl>decahydro-5'-methyl-4'-oxospiropyran>-6-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: Jones reagent / acetone / 0.5 h / 0 °C

2: 1.) cupric acetate monohydrate 2.) lead tetraacetate / pyridine / 1.) 0.5 h, room temperature 2a.) 1 h, 23 deg C 2b.) 2 h, 80 deg C

3: LDA / 1.) -78 deg C, 1 h 2.) -40 deg C, 2 h

4: anhydrous zinc chloride

5: 1.) ozone 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C 2.) 23 deg, 26 h

6: 1.) Jones reagent 2.) CH₂N₂ / 1a.) acetone, -10 deg C, 20 min 1b.) -5 deg C

With diazomethane; lead(IV) acetate; jones reagent; dimethylsulfide; copper diacetate; ozone; zinc(II) chloride; lithium diisopropyl amide; pyridine; In acetone;
DOI:10.1021/jo00179a018