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

Base Information

Chemical Name:4S,5S-2-(N-benzyloxycarbonyl)amino-5,6-dihydroxy-6-O-methanesulphonyl-hex-2-en-4-olide
CAS No.:108428-46-2
Molecular Formula:C₁₅H₁₇NO₈S
Molecular Weight:371.368
Hs Code.:

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

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

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

There total 6 articles about 4S,5S-2-(N-benzyloxycarbonyl)amino-5,6-dihydroxy-6-O-methanesulphonyl-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: 80.0%

: 124-63-0
methanesulfonyl chloride

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

: 108428-46-2
4S,5S-2-(N-benzyloxycarbonyl)amino-5,6-dihydroxy-6-O-methanesulphonyl-hex-2-en-4-olide

Guidance literature:: With pyridine; at -15 ℃; for 0.5h;
DOI:10.1016/S0040-4020(01)89973-7

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

: 108428-46-2
4S,5S-2-(N-benzyloxycarbonyl)amino-5,6-dihydroxy-6-O-methanesulphonyl-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: 80 percent / pyridine / 30 h / -20 °C

With sodium tetrahydroborate; sodium azide; hydrogen; sodium methylate; palladium on activated charcoal; In pyridine; 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

: 108428-46-2
4S,5S-2-(N-benzyloxycarbonyl)amino-5,6-dihydroxy-6-O-methanesulphonyl-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: 80 percent / pyridine / 30 h / -20 °C

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