2S,4S,5S-2-(N-benzyloxycarbonyl)amino-6-O-tert-butyldimethylsilyl-5,6-dihydroxy-hexan-4-olide

Base Information

• Chemical Name: 2S,4S,5S-2-(N-benzyloxycarbonyl)amino-6-O-tert-butyldimethylsilyl-5,6-dihydroxy-hexan-4-olide
• CAS No.: 108428-49-5
• Molecular Formula: C₂₀H₃₁NO₆Si
• Molecular Weight: 409.555

Synonyms:2S,4S,5S-2-(N-benzyloxycarbonyl)amino-6-O-tert-butyldimethylsilyl-5,6-dihydroxy-hexan-4-olide

Chemical Property of 2S,4S,5S-2-(N-benzyloxycarbonyl)amino-6-O-tert-butyldimethylsilyl-5,6-dihydroxy-hexan-4-olide

Chemical Property:

Purity/Quality:

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• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of 2S,4S,5S-2-(N-benzyloxycarbonyl)amino-6-O-tert-butyldimethylsilyl-5,6-dihydroxy-hexan-4-olide

There total 8 articles about 2S,4S,5S-2-(N-benzyloxycarbonyl)amino-6-O-tert-butyldimethylsilyl-5,6-dihydroxy-hexan-4-olide 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:

4S,5S-2-(N-benzyloxycarbonyl)amino-5,6-dihydroxyhex-2-en-4-olide (108428-45-1) → 2S,4S,5S-2-(N-benzyloxycarbonyl)amino-6-O-tert-butyldimethylsilyl-5,6-dihydroxy-hexan-4-olide (108428-49-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / Et₃N, dimethylamino pyridine / dimethylformamide; CH₂Cl₂

2: H₂ / Pd black / ethyl acetate; pyridine / 24 h / 20 °C

3: NaHCO₃ / ethyl acetate; H₂O / 1 h

With dmap; hydrogen; sodium hydrogencarbonate; triethylamine; palladium; In pyridine; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)84755-3

Reference yield:

4S,5S-2-(N-benzyloxycarbonyl)amino-5,6-dihydroxy-6-O-tert-butyldimethylsilyl-hex-2-en-4-olide (108428-48-4) → 2S,4S,5S-2-(N-benzyloxycarbonyl)amino-6-O-tert-butyldimethylsilyl-5,6-dihydroxy-hexan-4-olide (108428-49-5)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / Pd black / ethyl acetate; pyridine / 24 h / 20 °C

2: NaHCO₃ / ethyl acetate; H₂O / 1 h

With hydrogen; sodium hydrogencarbonate; palladium; In pyridine; water; ethyl acetate;

DOI:10.1016/S0040-4039(00)84755-3

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) + (3S,5S)-3-Amino-5-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-dihydro-furan-2-one → 2S,4S,5S-2-(N-benzyloxycarbonyl)amino-6-O-tert-butyldimethylsilyl-5,6-dihydroxy-hexan-4-olide (108428-49-5)

Guidance literature:

With sodium hydrogencarbonate; In ethyl acetate; at 0 ℃; for 1h; Yield given;

DOI:10.1016/S0040-4020(01)89973-7

upstream raw materials:

benzyl chloroformate

Trifluoro-methanesulfonic acid (3aR,6S,7aR)-2,2-dimethyl-5-oxo-hexahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxol-6-yl ester

isopropylidene glucuronolactone

4S,5S-2-(N-benzyloxycarbonyl)amino-5,6-dihydroxyhex-2-en-4-olide

Downstream raw materials:

2S,4S,5S-2-(N-benzyloxycarbonyl)amino-6-O-tert-butyldimethylsilyl-5,6-dihydroxy-5-O-methanesulphonyl-hexan-4-olide

(2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)pyrrolidine-2-carboxylic acid

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