<2R,3S,5S,5(4R)>-5-<2-(iodomethyl)tetrahydrofuran-4-yl>-5-<(4-methoxybenzyl)oxy>-2-methyl-3-<(triisopropylsilyl)oxy>pentanal

Base Information

Chemical Name:<2R,3S,5S,5(4R)>-5-<2-(iodomethyl)tetrahydrofuran-4-yl>-5-<(4-methoxybenzyl)oxy>-2-methyl-3-<(triisopropylsilyl)oxy>pentanal
CAS No.:128708-25-8
Molecular Formula:C₂₈H₄₇IO₅Si
Molecular Weight:618.668
Hs Code.:

Synonyms:<2R,3S,5S,5(4R)>-5-<2-(iodomethyl)tetrahydrofuran-4-yl>-5-<(4-methoxybenzyl)oxy>-2-methyl-3-<(triisopropylsilyl)oxy>pentanal

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Chemical Property of <2R,3S,5S,5(4R)>-5-<2-(iodomethyl)tetrahydrofuran-4-yl>-5-<(4-methoxybenzyl)oxy>-2-methyl-3-<(triisopropylsilyl)oxy>pentanal

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Technology Process of <2R,3S,5S,5(4R)>-5-<2-(iodomethyl)tetrahydrofuran-4-yl>-5-<(4-methoxybenzyl)oxy>-2-methyl-3-<(triisopropylsilyl)oxy>pentanal

There total 11 articles about <2R,3S,5S,5(4R)>-5-<2-(iodomethyl)tetrahydrofuran-4-yl>-5-<(4-methoxybenzyl)oxy>-2-methyl-3-<(triisopropylsilyl)oxy>pentanal 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

: 128708-25-8
<2R,3S,5S,5(4R)>-5-<2-(iodomethyl)tetrahydrofuran-4-yl>-5-<(4-methoxybenzyl)oxy>-2-methyl-3-<(triisopropylsilyl)oxy>pentanal

Guidance literature:: Multi-step reaction with 2 steps

1: Et₃N / CH₂Cl₂ / 3 h / Ambient temperature

2: 1.) O₃, pyridine, 2.) Me₂S / 1.) MeOH, CH₂Cl₂, -78 deg C, 2.) RT, 13 h

With pyridine; dimethylsulfide; ozone; triethylamine; In dichloromethane;
DOI:10.1021/ja00170a024

Reference yield:

: 128684-79-7
(3S,4R)-3-hydroxy-4-(hydroxymethyl)-1-<(4-methoxybenzyl)oxy>hept-6-ene

: 128708-25-8
<2R,3S,5S,5(4R)>-5-<2-(iodomethyl)tetrahydrofuran-4-yl>-5-<(4-methoxybenzyl)oxy>-2-methyl-3-<(triisopropylsilyl)oxy>pentanal

Guidance literature:: Multi-step reaction with 7 steps

1: 82 percent / DDQ, activated 3A molecular sieves / CH₂Cl₂ / 3 h / Ambient temperature

2: NaHCO₃, N-iodosuccinimide / acetonitrile / 1.) 0 deg C, 1 h, 2.) RT, 1 h

3: DIBAL-H / CH₂Cl₂ / 2 h / -78 - 20 °C

4: 94 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 0.5 h / -78 °C

5: 54 percent / BF₃*OEt₂ / CH₂Cl₂ / 1.67 h / -78 °C

6: Et₃N / CH₂Cl₂ / 3 h / Ambient temperature

7: 1.) O₃, pyridine, 2.) Me₂S / 1.) MeOH, CH₂Cl₂, -78 deg C, 2.) RT, 13 h

With pyridine; N-iodo-succinimide; oxalyl dichloride; dimethylsulfide; 3 A molecular sieve; boron trifluoride diethyl etherate; diisobutylaluminium hydride; sodium hydrogencarbonate; ozone; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; acetonitrile;
DOI:10.1021/ja00170a024

Reference yield:

: 128684-80-0,128708-06-5
<3S,3(2RS,4R)>-3-<(4-methoxybenzyl)oxy>-3-<2-(iodomethyl)tetrahydrofuran-4-yl>propan-1-ol

: 128708-25-8
<2R,3S,5S,5(4R)>-5-<2-(iodomethyl)tetrahydrofuran-4-yl>-5-<(4-methoxybenzyl)oxy>-2-methyl-3-<(triisopropylsilyl)oxy>pentanal

Guidance literature:: Multi-step reaction with 4 steps

1: 94 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 0.5 h / -78 °C

2: 54 percent / BF₃*OEt₂ / CH₂Cl₂ / 1.67 h / -78 °C

3: Et₃N / CH₂Cl₂ / 3 h / Ambient temperature

4: 1.) O₃, pyridine, 2.) Me₂S / 1.) MeOH, CH₂Cl₂, -78 deg C, 2.) RT, 13 h

With pyridine; oxalyl dichloride; dimethylsulfide; boron trifluoride diethyl etherate; ozone; dimethyl sulfoxide; triethylamine; In dichloromethane;
DOI:10.1021/ja00170a024