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

Base Information

Chemical Name:4S,5S-2-(N-benzyloxycarbonyl)amino-5,6-dihydroxy-6-O-tert-butyldimethylsilyl-hex-2-en-4-olide
CAS No.:108428-48-4
Molecular Formula:C₂₀H₂₉NO₆Si
Molecular Weight:407.539
Hs Code.:

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

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

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

There total 6 articles about 4S,5S-2-(N-benzyloxycarbonyl)amino-5,6-dihydroxy-6-O-tert-butyldimethylsilyl-hex-2-en-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: 92.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 108428-45-1
4S,5S-2-(N-benzyloxycarbonyl)amino-5,6-dihydroxyhex-2-en-4-olide

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

Guidance literature:: With dmap; triethylamine; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)84755-3

Reference yield:

: 76542-57-9,103357-81-9
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

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

Guidance literature:: Multi-step reaction with 4 steps

1: 84 percent / NaN₃ / dimethylformamide / 5 h / -20 °C

2: H₂ / Pd/C / ethyl acetate / 3 h / 20 °C

3: 1.) MeONa; 2.) NaBH₄ / 1.) MeOH, 0 deg C, 1 min; 2.) MeOH, 0 deg C, 5 min

4: 92 percent / Et₃N, dimethylamino pyridine / dimethylformamide; CH₂Cl₂

With dmap; sodium tetrahydroborate; sodium azide; hydrogen; sodium methylate; triethylamine; palladium on activated charcoal; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)84755-3

Reference yield:

: 3067-56-9,20513-98-8,25159-39-1,26623-22-3,29514-28-1,85080-95-1
isopropylidene glucuronolactone

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

Guidance literature:: Multi-step reaction with 5 steps

1: pyridine / CH₂Cl₂ / -30 °C

2: 84 percent / NaN₃ / dimethylformamide / 5 h / -20 °C

3: H₂ / Pd/C / ethyl acetate / 3 h / 20 °C

4: 1.) MeONa; 2.) NaBH₄ / 1.) MeOH, 0 deg C, 1 min; 2.) MeOH, 0 deg C, 5 min

5: 92 percent / Et₃N, dimethylamino pyridine / dimethylformamide; CH₂Cl₂

With pyridine; dmap; sodium tetrahydroborate; sodium azide; hydrogen; sodium methylate; triethylamine; palladium on activated charcoal; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)84755-3