2(R)-ethyl-2-<5(R)-(hydroxymethyl)-3(S)-methyl-2(R)-tetrahydrofuryl>-3(R),4(S)-<(dimethylmethylene)dioxy>-5(S)-(benzyloxy)tetrahydrofuran

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Chemical Name:2(R)-ethyl-2-<5(R)-(hydroxymethyl)-3(S)-methyl-2(R)-tetrahydrofuryl>-3(R),4(S)-<(dimethylmethylene)dioxy>-5(S)-(benzyloxy)tetrahydrofuran
CAS No.:150019-30-0
Molecular Formula:C₂₂H₃₂O₆
Molecular Weight:392.492
Hs Code.:

Synonyms:2(R)-ethyl-2-<5(R)-(hydroxymethyl)-3(S)-methyl-2(R)-tetrahydrofuryl>-3(R),4(S)-<(dimethylmethylene)dioxy>-5(S)-(benzyloxy)tetrahydrofuran

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Chemical Property of 2(R)-ethyl-2-<5(R)-(hydroxymethyl)-3(S)-methyl-2(R)-tetrahydrofuryl>-3(R),4(S)-<(dimethylmethylene)dioxy>-5(S)-(benzyloxy)tetrahydrofuran

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Technology Process of 2(R)-ethyl-2-<5(R)-(hydroxymethyl)-3(S)-methyl-2(R)-tetrahydrofuryl>-3(R),4(S)-<(dimethylmethylene)dioxy>-5(S)-(benzyloxy)tetrahydrofuran

There total 6 articles about 2(R)-ethyl-2-<5(R)-(hydroxymethyl)-3(S)-methyl-2(R)-tetrahydrofuryl>-3(R),4(S)-<(dimethylmethylene)dioxy>-5(S)-(benzyloxy)tetrahydrofuran 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: 96.0%

: 2(R)-vinyl-2-<2,5-dihydro-5(R)-(hydroxymethyl)-3-methyl-2(R)-furyl>-3(R),4(S)-<(dimethylmethylene)dioxy>-5(S)-(benzyloxy)tetrahydrofuran

: 150019-30-0
2(R)-ethyl-2-<5(R)-(hydroxymethyl)-3(S)-methyl-2(R)-tetrahydrofuryl>-3(R),4(S)-<(dimethylmethylene)dioxy>-5(S)-(benzyloxy)tetrahydrofuran

Guidance literature:: With [(bicyclo[2.2.1]hepta-2,5-diene)(1,4-bis(diphenylphosphino)butane)rhodium(I)] tetrafluoroborate; hydrogen; In dichloromethane; for 2h; under 33097.5 Torr;
DOI:10.1021/ja00069a013

Reference yield:

: 96150-86-6
benzyl 2,3-O-(1-methylethylidene)-α-D-lyxofuranosiduronic acid chloride

: 150019-30-0
2(R)-ethyl-2-<5(R)-(hydroxymethyl)-3(S)-methyl-2(R)-tetrahydrofuryl>-3(R),4(S)-<(dimethylmethylene)dioxy>-5(S)-(benzyloxy)tetrahydrofuran

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) TMSCl, HMPA, 2.) LDA, 3.) LAH / 1.) -100 deg C, 2.) RT

2: 88 percent / Dess-Martin reagent

3: 70 percent

4: 94 percent / CsF / hexamethylphosphoric acid triamide / 15 h / 125 °C

5: 96 percent / H₂, BF₄ / CH₂Cl₂ / 2 h / 33097.5 Torr

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; chloro-trimethyl-silane; [(bicyclo[2.2.1]hepta-2,5-diene)(1,4-bis(diphenylphosphino)butane)rhodium(I)] tetrafluoroborate; hydrogen; Dess-Martin periodane; cesium fluoride; lithium diisopropyl amide; In N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane;
DOI:10.1021/ja00069a013

Reference yield:

: (3aR,4R,6S,6aS)-6-Benzyloxy-2,2-dimethyl-4-[(2R,5R)-3-methyl-5-(2-trimethylsilanyl-ethoxymethoxymethyl)-2,5-dihydro-furan-2-yl]-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbaldehyde

: 150019-30-0
2(R)-ethyl-2-<5(R)-(hydroxymethyl)-3(S)-methyl-2(R)-tetrahydrofuryl>-3(R),4(S)-<(dimethylmethylene)dioxy>-5(S)-(benzyloxy)tetrahydrofuran

Guidance literature:: Multi-step reaction with 3 steps

1: 70 percent

2: 94 percent / CsF / hexamethylphosphoric acid triamide / 15 h / 125 °C

3: 96 percent / H₂, BF₄ / CH₂Cl₂ / 2 h / 33097.5 Torr

With [(bicyclo[2.2.1]hepta-2,5-diene)(1,4-bis(diphenylphosphino)butane)rhodium(I)] tetrafluoroborate; hydrogen; cesium fluoride; In N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane;
DOI:10.1021/ja00069a013