2-[(Z)-(2S,3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-7-iodo-3,5-dimethyl-2-triisopropylsilanyloxy-hept-5-enyl]-[1,3]dioxolane

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Chemical Name:2-[(Z)-(2S,3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-7-iodo-3,5-dimethyl-2-triisopropylsilanyloxy-hept-5-enyl]-[1,3]dioxolane
CAS No.:161926-55-2
Molecular Formula:C₂₇H₅₅IO₄Si₂
Molecular Weight:626.807
Hs Code.:

Synonyms:2-[(Z)-(2S,3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-7-iodo-3,5-dimethyl-2-triisopropylsilanyloxy-hept-5-enyl]-[1,3]dioxolane

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Chemical Property of 2-[(Z)-(2S,3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-7-iodo-3,5-dimethyl-2-triisopropylsilanyloxy-hept-5-enyl]-[1,3]dioxolane

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Technology Process of 2-[(Z)-(2S,3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-7-iodo-3,5-dimethyl-2-triisopropylsilanyloxy-hept-5-enyl]-[1,3]dioxolane

There total 1 articles about 2-[(Z)-(2S,3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-7-iodo-3,5-dimethyl-2-triisopropylsilanyloxy-hept-5-enyl]-[1,3]dioxolane 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

: 161926-55-2
2-[(Z)-(2S,3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-7-iodo-3,5-dimethyl-2-triisopropylsilanyloxy-hept-5-enyl]-[1,3]dioxolane

Guidance literature:: Multi-step reaction with 9 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

7: 90 percent

8: 85 percent / HF*Pyr

9: 82 percent / methyltriphenoxyphosphonium iodide / dimethylformamide / 0.5 h / 0 - 20 °C

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

Reference yield: 80.0%

: 161926-57-4
1-(3-[1,3]Dithian-2-yl-2,5-dimethoxy-phenyl)-2,5-dimethyl-1H-pyrrole

: 161926-55-2
2-[(Z)-(2S,3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-7-iodo-3,5-dimethyl-2-triisopropylsilanyloxy-hept-5-enyl]-[1,3]dioxolane

: 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:: With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 1.5h;
DOI:10.1016/0040-4039(94)02427-D

Reference yield:

: 161926-55-2
2-[(Z)-(2S,3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-7-iodo-3,5-dimethyl-2-triisopropylsilanyloxy-hept-5-enyl]-[1,3]dioxolane

: 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 2 steps

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

2: 98 percent / H₂ / Raney-Ni / ethanol / 0.17 h

With n-butyllithium; hydrogen; nickel; In ethanol;
DOI:10.1021/ja9743194