2(R)-ethyl-2-<5(R)-<2(S)-methyl-1(S)-<(triethylsilyl)oxy>-3-butenyl>-3(S)-methyl-2(R)-tetrahydrofuryl>-3(R),4(S)-<(dimethylmethylene)dioxy>-5(S)-(benzyloxy)tetrahydrofuran

Base Information

Chemical Name:2(R)-ethyl-2-<5(R)-<2(S)-methyl-1(S)-<(triethylsilyl)oxy>-3-butenyl>-3(S)-methyl-2(R)-tetrahydrofuryl>-3(R),4(S)-<(dimethylmethylene)dioxy>-5(S)-(benzyloxy)tetrahydrofuran
CAS No.:150019-31-1
Molecular Formula:C₃₂H₅₂O₆Si
Molecular Weight:560.847
Hs Code.:

2(R)-ethyl-2-<5(R)-<2(S)-methyl-1(S)-<(triethylsilyl)oxy>-3-butenyl>-3(S)-methyl-2(R)-tetrahydrofuryl>-3(R),4(S)-<(dimethylmethylene)dioxy>-5(S)-(benzyloxy)tetrahydrofuran

Synonyms:2(R)-ethyl-2-<5(R)-<2(S)-methyl-1(S)-<(triethylsilyl)oxy>-3-butenyl>-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)-<2(S)-methyl-1(S)-<(triethylsilyl)oxy>-3-butenyl>-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)-<2(S)-methyl-1(S)-<(triethylsilyl)oxy>-3-butenyl>-3(S)-methyl-2(R)-tetrahydrofuryl>-3(R),4(S)-<(dimethylmethylene)dioxy>-5(S)-(benzyloxy)tetrahydrofuran

There total 9 articles about 2(R)-ethyl-2-<5(R)-<2(S)-methyl-1(S)-<(triethylsilyl)oxy>-3-butenyl>-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:

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

: 150019-31-1
2(R)-ethyl-2-<5(R)-<2(S)-methyl-1(S)-<(triethylsilyl)oxy>-3-butenyl>-3(S)-methyl-2(R)-tetrahydrofuryl>-3(R),4(S)-<(dimethylmethylene)dioxy>-5(S)-(benzyloxy)tetrahydrofuran

Guidance literature:: Multi-step reaction with 8 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

6: Dess-Martin periodinane / CH₂Cl₂ / 4 h

7: 1.) t-BuOK, n-BuLi, 2.) (-)-B-methoxydiisopinocampheylborane, BF₃*OEt₂, 3.) 3 N aq. NaOH, 30percent aq. H₂O₂

8: 2,6-lutidine / CH₂Cl₂ / 1 h

With (-)-B-methoxydiisopinocamphenylborane; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; chloro-trimethyl-silane; [(bicyclo[2.2.1]hepta-2,5-diene)(1,4-bis(diphenylphosphino)butane)rhodium(I)] tetrafluoroborate; boron trifluoride diethyl etherate; potassium tert-butylate; hydrogen; dihydrogen peroxide; Dess-Martin periodane; cesium fluoride; lithium diisopropyl amide; In N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane;
DOI:10.1021/ja00069a013

Reference yield:

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

: 150019-31-1
2(R)-ethyl-2-<5(R)-<2(S)-methyl-1(S)-<(triethylsilyl)oxy>-3-butenyl>-3(S)-methyl-2(R)-tetrahydrofuryl>-3(R),4(S)-<(dimethylmethylene)dioxy>-5(S)-(benzyloxy)tetrahydrofuran

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) t-BuOK, n-BuLi, 2.) (-)-B-methoxydiisopinocampheylborane, BF₃*OEt₂, 3.) 3 N aq. NaOH, 30percent aq. H₂O₂

2: 2,6-lutidine / CH₂Cl₂ / 1 h

With (-)-B-methoxydiisopinocamphenylborane; 2,6-dimethylpyridine; sodium hydroxide; n-butyllithium; boron trifluoride diethyl etherate; potassium tert-butylate; dihydrogen peroxide; In dichloromethane;
DOI:10.1021/ja00069a013

Reference yield:

: 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

: 150019-31-1
2(R)-ethyl-2-<5(R)-<2(S)-methyl-1(S)-<(triethylsilyl)oxy>-3-butenyl>-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: Dess-Martin periodinane / CH₂Cl₂ / 4 h

2: 1.) t-BuOK, n-BuLi, 2.) (-)-B-methoxydiisopinocampheylborane, BF₃*OEt₂, 3.) 3 N aq. NaOH, 30percent aq. H₂O₂

3: 2,6-lutidine / CH₂Cl₂ / 1 h

With (-)-B-methoxydiisopinocamphenylborane; 2,6-dimethylpyridine; sodium hydroxide; n-butyllithium; boron trifluoride diethyl etherate; potassium tert-butylate; dihydrogen peroxide; Dess-Martin periodane; In dichloromethane;
DOI:10.1021/ja00069a013