<3S,4S,6S,6(4R)>-6-<2-(iodomethyl)tetrahydrofuran-4-yl>-6-<(4-methoxybenzyl)oxy>-3-methyl-4-<(triisopropylsilyl)oxy>-1-hexene

Base Information

• Chemical Name: <3S,4S,6S,6(4R)>-6-<2-(iodomethyl)tetrahydrofuran-4-yl>-6-<(4-methoxybenzyl)oxy>-3-methyl-4-<(triisopropylsilyl)oxy>-1-hexene
• CAS No.: 128684-92-4
• Molecular Formula: C₂₉H₄₉IO₄Si
• Molecular Weight: 616.696
• Mol file: 128684-92-4.mol

Synonyms:<3S,4S,6S,6(4R)>-6-<2-(iodomethyl)tetrahydrofuran-4-yl>-6-<(4-methoxybenzyl)oxy>-3-methyl-4-<(triisopropylsilyl)oxy>-1-hexene

Chemical Property of <3S,4S,6S,6(4R)>-6-<2-(iodomethyl)tetrahydrofuran-4-yl>-6-<(4-methoxybenzyl)oxy>-3-methyl-4-<(triisopropylsilyl)oxy>-1-hexene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <3S,4S,6S,6(4R)>-6-<2-(iodomethyl)tetrahydrofuran-4-yl>-6-<(4-methoxybenzyl)oxy>-3-methyl-4-<(triisopropylsilyl)oxy>-1-hexene

There total 9 articles about <3S,4S,6S,6(4R)>-6-<2-(iodomethyl)tetrahydrofuran-4-yl>-6-<(4-methoxybenzyl)oxy>-3-methyl-4-<(triisopropylsilyl)oxy>-1-hexene 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:

(3S,4R)-3-hydroxy-4-(hydroxymethyl)-1-<(4-methoxybenzyl)oxy>hept-6-ene (128684-79-7) → <3S,4S,6S,6(4R)>-6-<2-(iodomethyl)tetrahydrofuran-4-yl>-6-<(4-methoxybenzyl)oxy>-3-methyl-4-<(triisopropylsilyl)oxy>-1-hexene (128684-92-4)

Guidance literature:

Multi-step reaction with 6 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

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

DOI:10.1021/ja00170a024

Reference yield:

<3S,3(2RS,4R)>-3-<(4-methoxybenzyl)oxy>-3-<2-(iodomethyl)tetrahydrofuran-4-yl>propan-1-ol (128684-80-0,128708-06-5) → <3S,4S,6S,6(4R)>-6-<2-(iodomethyl)tetrahydrofuran-4-yl>-6-<(4-methoxybenzyl)oxy>-3-methyl-4-<(triisopropylsilyl)oxy>-1-hexene (128684-92-4)

Guidance literature:

Multi-step reaction with 3 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

With oxalyl dichloride; boron trifluoride diethyl etherate; dimethyl sulfoxide; triethylamine; In dichloromethane;

DOI:10.1021/ja00170a024

Reference yield:

methyl (3S)-3-hydroxy-5-<(4-methoxybenzyl)oxy>pentanoate (128684-78-6) → <3S,4S,6S,6(4R)>-6-<2-(iodomethyl)tetrahydrofuran-4-yl>-6-<(4-methoxybenzyl)oxy>-3-methyl-4-<(triisopropylsilyl)oxy>-1-hexene (128684-92-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) LDA / 1.) THF, ether, -78 deg C, 1 h, 2.) HMPA, from -78 deg C to 0 deg C, 240 min

2: 90 percent / LiAlH₄ / tetrahydrofuran / 1.) 0 deg C, 3 h, 2.) RT, 1 h

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

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

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

6: 94 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 0.5 h / -78 °C

7: 54 percent / BF₃*OEt₂ / CH₂Cl₂ / 1.67 h / -78 °C

8: Et₃N / CH₂Cl₂ / 3 h / Ambient temperature

With N-iodo-succinimide; lithium aluminium tetrahydride; oxalyl dichloride; 3 A molecular sieve; boron trifluoride diethyl etherate; diisobutylaluminium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1021/ja00170a024

upstream raw materials:

triisopropylsilyl trifluoromethanesulfonate

<3S,4S,6S,6(4R)>-4-hydroxy-6-<(4-methoxybenzyl)oxy>-3-methyl-6-<2-(iodomethyl)tetrahydrofuran-4-yl>hex-1-ene

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

<3S,3(2RS,4R)>-3-<(4-methoxybenzyl)oxy>-3-<2-(iodomethyl)tetrahydrofuran-4-yl>propan-1-ol

Downstream raw materials:

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

<1(1R,3R,4R),1E,3(2S),3S,4S,5S,7S,8S>-3--7-<(4-methoxybenzyl)oxy>-1-<3-methoxy-4-<(triisopropylsilyl)oxy>cyclohex-1-yl>-2,4-dimethyl-8-(2-propen-1-yl)-5-<(triisopropylsilyl)oxy>-1-nonen-9-al

<1(1R,3R,4R),1E,3(2S),3S,4S,5S,7S,8R>-3--2,4-dimethyl-8-(hydroxymethyl)-7-<(4-methoxybenzyl)oxy>-1-<3-methoxy-4-<(triisopropylsilyl)oxy>cyclohex-1-yl>-5-<(triisopropylsilyl)oxy>-1,10-undecadiene

C₅₈H₁₀₂INO₁₀Si₂