(1S,6R)-6-<(tert-butyldimethylsilyl)oxy>-1-<(1S,2S)-2,3-dihydroxy-2,3-O-isopropylidene-1-(p-methoxybenzyl)-2-methylpropyl>-7,9-bis(p-methoxybenzyl)-5-methylene-7,9-diaza-2-oxabicyclo<4.2.2>decane-8,10-dione

Base Information

• Chemical Name: (1S,6R)-6-<(tert-butyldimethylsilyl)oxy>-1-<(1S,2S)-2,3-dihydroxy-2,3-O-isopropylidene-1-(p-methoxybenzyl)-2-methylpropyl>-7,9-bis(p-methoxybenzyl)-5-methylene-7,9-diaza-2-oxabicyclo<4.2.2>decane-8,10-dione
• CAS No.: 117183-89-8
• Molecular Formula: C₄₅H₆₀N₂O₁₀Si
• Molecular Weight: 817.064

Synonyms:(1S,6R)-6-<(tert-butyldimethylsilyl)oxy>-1-<(1S,2S)-2,3-dihydroxy-2,3-O-isopropylidene-1-(p-methoxybenzyl)-2-methylpropyl>-7,9-bis(p-methoxybenzyl)-5-methylene-7,9-diaza-2-oxabicyclo<4.2.2>decane-8,10-dione

Chemical Property of (1S,6R)-6-<(tert-butyldimethylsilyl)oxy>-1-<(1S,2S)-2,3-dihydroxy-2,3-O-isopropylidene-1-(p-methoxybenzyl)-2-methylpropyl>-7,9-bis(p-methoxybenzyl)-5-methylene-7,9-diaza-2-oxabicyclo<4.2.2>decane-8,10-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

Technology Process of (1S,6R)-6-<(tert-butyldimethylsilyl)oxy>-1-<(1S,2S)-2,3-dihydroxy-2,3-O-isopropylidene-1-(p-methoxybenzyl)-2-methylpropyl>-7,9-bis(p-methoxybenzyl)-5-methylene-7,9-diaza-2-oxabicyclo<4.2.2>decane-8,10-dione

There total 5 articles about (1S,6R)-6-<(tert-butyldimethylsilyl)oxy>-1-<(1S,2S)-2,3-dihydroxy-2,3-O-isopropylidene-1-(p-methoxybenzyl)-2-methylpropyl>-7,9-bis(p-methoxybenzyl)-5-methylene-7,9-diaza-2-oxabicyclo<4.2.2>decane-8,10-dione 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:

(1S,6R)-6-<(tert-butyldimethylsilyl)oxy>-1-<(1S,2S)-2,3-O-isopropylidene-2-methyl-1,2,3-trihydroxypropyl>-7,9-bis(p-methoxybenzyl)-5-methylene-7,9-diaza-2-oxabicyclo<4.2.2>decane-8,10-dione (95237-55-1) → (1S,6R)-6-<(tert-butyldimethylsilyl)oxy>-1-<(1S,2S)-2,3-dihydroxy-2,3-O-isopropylidene-1-(p-methoxybenzyl)-2-methylpropyl>-7,9-bis(p-methoxybenzyl)-5-methylene-7,9-diaza-2-oxabicyclo<4.2.2>decane-8,10-dione (117183-89-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 49 percent / CAN / acetonitrile / 0.42 h

2: 100 percent / PPTS / acetone / 12 h / Ambient temperature

3: 1.) NaH / 1.) DMF, 2.) 2 h

With ammonium cerium(IV) nitrate; pyridinium p-toluenesulfonate; sodium hydride; In acetone; acetonitrile;

DOI:10.1021/jo00261a009

Reference yield:

(1S,6R)-6-(tert-butyldimethylsilyl)-7,9-bis(p-methoxybenzyl)-5-methylene-7,9-diaza-2-oxabicyclo<4.2.2>decane-8,10-dione (117249-39-5) → (1S,6R)-6-<(tert-butyldimethylsilyl)oxy>-1-<(1S,2S)-2,3-dihydroxy-2,3-O-isopropylidene-1-(p-methoxybenzyl)-2-methylpropyl>-7,9-bis(p-methoxybenzyl)-5-methylene-7,9-diaza-2-oxabicyclo<4.2.2>decane-8,10-dione (117183-89-8)

Guidance literature:

Multi-step reaction with 4 steps

1: BuLi / tetrahydrofuran / -100 °C

2: 49 percent / CAN / acetonitrile / 0.42 h

3: 100 percent / PPTS / acetone / 12 h / Ambient temperature

4: 1.) NaH / 1.) DMF, 2.) 2 h

With n-butyllithium; ammonium cerium(IV) nitrate; pyridinium p-toluenesulfonate; sodium hydride; In tetrahydrofuran; acetone; acetonitrile;

DOI:10.1021/jo00261a009

Reference yield:

(S)-(-)-2,2,4-trimethyl-1,3-dioxolane-4-carboxaldehyde (79243-92-8) → (1S,6R)-6-<(tert-butyldimethylsilyl)oxy>-1-<(1S,2S)-2,3-dihydroxy-2,3-O-isopropylidene-1-(p-methoxybenzyl)-2-methylpropyl>-7,9-bis(p-methoxybenzyl)-5-methylene-7,9-diaza-2-oxabicyclo<4.2.2>decane-8,10-dione (117183-89-8)

Guidance literature:

Multi-step reaction with 3 steps

1: BuLi / tetrahydrofuran / -100 °C

2: 4.8 percent / CAN / acetonitrile / 0.42 h

3: 1.) NaH / 1.) DMF, 2.) 2 h

With n-butyllithium; ammonium cerium(IV) nitrate; sodium hydride; In tetrahydrofuran; acetonitrile;

DOI:10.1021/jo00261a009

upstream raw materials:

p-Methoxybenzyl bromide

(1S,6R)-6-<(tert-butyldimethylsilyl)oxy>-1-<(1S,2S)-2,3-O-isopropylidene-2-methyl-1,2,3-trihydroxypropyl>-5-methylene-7,9-diaza-2-oxabicyclo<4.2.2>decane-8,10-dione

(S)-(-)-2,2,4-trimethyl-1,3-dioxolane-4-carboxaldehyde

(1S,6R)-6-<(tert-butyldimethylsilyl)oxy>-1-<(1S,2S)-2-methyl-1,2,3-trihydroxypropyl>-5-methylene-7,9-diaza-2-oxabicyclo<4.2.2>decane-8,10-dione

Downstream raw materials:

Aizumycin

Benzoic acid 3-[(3S,4S)-3,4,8-trihydroxy-6,9-bis-(4-methoxy-benzyl)-3-methyl-7,10-dioxo-1-oxa-6,9-diaza-spiro[4.5]dec-8-yl]-but-3-enyl ester

Benzoic acid (2S,3S)-2,3-dihydroxy-3-[(1S,6R)-6-hydroxy-7,9-bis-(4-methoxy-benzyl)-5-methylene-8,10-dioxo-2-oxa-7,9-diaza-bicyclo[4.2.2]dec-1-yl]-2-methyl-propyl ester

(1S,6R)-6-hydroxy-1-<(1S,2S)-2,3-O-isopropylidene-2-methyl-1,2,3-trihydroxypropyl>-7,9-bis(p-methoxybenzyl)-5-methylene-7,9-diaza-2-oxabicyclo<4.2.2>decane-8,10-dione

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