2(S)-ethyl-2-<5(S)-carboxy-3(S)-methyl-2(R)-tetrahydrofuryl>-3(R),4(S)-(dimethylmethylenedioxy)-5(S)-(benzyloxy)tetrahydrofuran

Base Information

Chemical Name:2(S)-ethyl-2-<5(S)-carboxy-3(S)-methyl-2(R)-tetrahydrofuryl>-3(R),4(S)-(dimethylmethylenedioxy)-5(S)-(benzyloxy)tetrahydrofuran
CAS No.:96150-95-7
Molecular Formula:C₂₂H₃₀O₇
Molecular Weight:406.476
Hs Code.:

Synonyms:2(S)-ethyl-2-<5(S)-carboxy-3(S)-methyl-2(R)-tetrahydrofuryl>-3(R),4(S)-(dimethylmethylenedioxy)-5(S)-(benzyloxy)tetrahydrofuran

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

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

There total 1 articles about 2(S)-ethyl-2-<5(S)-carboxy-3(S)-methyl-2(R)-tetrahydrofuryl>-3(R),4(S)-(dimethylmethylenedioxy)-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:

: 96150-93-5
2(S)-ethyl-2-<5(S)-(hydroxymethyl)-3(S)-methyl-2(R)-tetrahydrofuryl>-3(R),4(S)-(dimethylmethylenedioxy)-5(S)-(benzyloxy)tetrahydrofuran

: 96150-95-7
2(S)-ethyl-2-<5(S)-carboxy-3(S)-methyl-2(R)-tetrahydrofuryl>-3(R),4(S)-(dimethylmethylenedioxy)-5(S)-(benzyloxy)tetrahydrofuran

Guidance literature:: With potassium hydroxide; oxalyl dichloride; silver nitrate; dimethyl sulfoxide; triethylamine; Yield given. Multistep reaction; 1.) CH₂Cl₂, -78 deg C, 20 min; 2.) EtOH, H₂O, 30 min, room temp.;
DOI:10.1021/ja00297a038

Reference yield:

: 96150-95-7
2(S)-ethyl-2-<5(S)-carboxy-3(S)-methyl-2(R)-tetrahydrofuryl>-3(R),4(S)-(dimethylmethylenedioxy)-5(S)-(benzyloxy)tetrahydrofuran

: 2(S)-ethyl-<5(R)-carboxy-3(S)-methyl-2(R)-<2(S)-ethyl-3(R),4(S)-(dimethylmethylenedioxy)-5(S)-(benzyloxy)-2-tetrahydrofuryl>-5-tetrahydrofuryl>-3-methyl-5,6-dihydro-5(R)-methyl-6(S)-methoxy-6-<(<(1,1-dimethylethyl)dimethylsilyl>oxy)methyl>-2H-pyran ph..

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) CCl₄, PPh₃; 2.) DMAP / 1.) CH₂Cl₂, 50 deg C, 2 h; 2.) CH₂Cl₂, room temp., 20 min

2: 45 percent / LDA, TMSCl, Et₃N / tetrahydrofuran / 2 h / 50 °C

3: 80 percent / phenyl dichlorophosphate, Et₃N / tetrahydrofuran / 0.17 h / 0 °C

With tetrachloromethane; dmap; chloro-trimethyl-silane; O-phenyl phosphorodichloridate; triethylamine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran;
DOI:10.1021/ja00297a039

Reference yield:

: 96150-95-7
2(S)-ethyl-2-<5(S)-carboxy-3(S)-methyl-2(R)-tetrahydrofuryl>-3(R),4(S)-(dimethylmethylenedioxy)-5(S)-(benzyloxy)tetrahydrofuran

: 96150-93-5
2(S)-ethyl-2-<5(S)-(hydroxymethyl)-3(S)-methyl-2(R)-tetrahydrofuryl>-3(R),4(S)-(dimethylmethylenedioxy)-5(S)-(benzyloxy)tetrahydrofuran

Guidance literature:: Multi-step reaction with 2 steps

1: diethyl ether

2: LiAlH₄ / diethyl ether / 0 °C

With lithium aluminium tetrahydride; In diethyl ether;
DOI:10.1021/ja00297a038