(Z)-(4R,5R,6S)-7-[1,3]Dioxolan-2-yl-3,5-dimethyl-6-triisopropylsilanyloxy-hept-2-ene-1,4-diol

Base Information

Chemical Name:(Z)-(4R,5R,6S)-7-[1,3]Dioxolan-2-yl-3,5-dimethyl-6-triisopropylsilanyloxy-hept-2-ene-1,4-diol
CAS No.:161926-52-9
Molecular Formula:C₂₁H₄₂O₅Si
Molecular Weight:402.647
Hs Code.:

Synonyms:(Z)-(4R,5R,6S)-7-[1,3]Dioxolan-2-yl-3,5-dimethyl-6-triisopropylsilanyloxy-hept-2-ene-1,4-diol

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Chemical Property of (Z)-(4R,5R,6S)-7-[1,3]Dioxolan-2-yl-3,5-dimethyl-6-triisopropylsilanyloxy-hept-2-ene-1,4-diol

Chemical Property:

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Technology Process of (Z)-(4R,5R,6S)-7-[1,3]Dioxolan-2-yl-3,5-dimethyl-6-triisopropylsilanyloxy-hept-2-ene-1,4-diol

There total 1 articles about (Z)-(4R,5R,6S)-7-[1,3]Dioxolan-2-yl-3,5-dimethyl-6-triisopropylsilanyloxy-hept-2-ene-1,4-diol 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:

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 161926-52-9
(Z)-(4R,5R,6S)-7-[1,3]Dioxolan-2-yl-3,5-dimethyl-6-triisopropylsilanyloxy-hept-2-ene-1,4-diol

Guidance literature:: Multi-step reaction with 6 steps

1: 100 percent

2: 1.) O₃, pyridine, 2.) Me₂S / 1.) MeOH, CH₂Cl₂, -78 deg C, 2.) MeOH, CH₂Cl₂, RT, 12 h

3: BF₃*EtO₂

4: 98 percent / H₂, TFA / 10percent Pd/C / ethanol / 24 h / 760 Torr

5: 94 percent / DBU / tetrahydrofuran / 0.5 h / 0 °C

6: 10 percent / LiALH₄ / diethyl ether / -15 °C

With pyridine; lithium aluminium tetrahydride; dimethylsulfide; boron trifluoride diethyl etherate; hydrogen; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol;
DOI:10.1021/ja9743194

Reference yield:

: 161926-52-9
(Z)-(4R,5R,6S)-7-[1,3]Dioxolan-2-yl-3,5-dimethyl-6-triisopropylsilanyloxy-hept-2-ene-1,4-diol

: 1-{3-[(Z)-(5R,6S,7S)-5-(tert-Butyl-dimethyl-silanyloxy)-8-[1,3]dioxolan-2-yl-4,6-dimethyl-7-triisopropylsilanyloxy-oct-3-enyl]-2,5-dimethoxy-phenyl}-2,5-dimethyl-1H-pyrrole

Guidance literature:: Multi-step reaction with 5 steps

1: 90 percent

2: 85 percent / HF*Pyr

3: 82 percent / methyltriphenoxyphosphonium iodide / dimethylformamide / 0.5 h / 0 - 20 °C

4: 1.) n-BuLi / 1.) THF, -78 deg C, 30 min, 2. ) THF, -78 deg C, 30 min

5: 98 percent / H₂ / Raney-Ni / ethanol / 0.17 h

With n-butyllithium; methyltriphenoxyphosphonium iodide; hydrogen; pyridine hydrogenfluoride; nickel; In ethanol; N,N-dimethyl-formamide;
DOI:10.1021/ja9743194

Reference yield:

: 161926-52-9
(Z)-(4R,5R,6S)-7-[1,3]Dioxolan-2-yl-3,5-dimethyl-6-triisopropylsilanyloxy-hept-2-ene-1,4-diol

: 161926-58-5
1-(3-{2-[(Z)-(4R,5S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-7-[1,3]dioxolan-2-yl-3,5-dimethyl-6-triisopropylsilanyloxy-hept-2-enyl]-[1,3]dithian-2-yl}-2,5-dimethoxy-phenyl)-2,5-dimethyl-1H-pyrrole

Guidance literature:: Multi-step reaction with 4 steps

1: 90 percent

2: 85 percent / HF*Pyr

3: 82 percent / methyltriphenoxyphosphonium iodide / dimethylformamide / 0.5 h / 0 - 20 °C

4: 1.) n-BuLi / 1.) THF, -78 deg C, 30 min, 2. ) THF, -78 deg C, 30 min

With n-butyllithium; methyltriphenoxyphosphonium iodide; pyridine hydrogenfluoride; In N,N-dimethyl-formamide;
DOI:10.1021/ja9743194