methyl (3S,4R,5R)-5-acetoxy-3-azido-4-hydroxycyclohex-1-ene-1-carboxylate

Base Information

Chemical Name:methyl (3S,4R,5R)-5-acetoxy-3-azido-4-hydroxycyclohex-1-ene-1-carboxylate
CAS No.:352533-29-0
Molecular Formula:C₁₀H₁₃N₃O₅
Molecular Weight:255.23
Hs Code.:

Synonyms:methyl (3S,4R,5R)-5-acetoxy-3-azido-4-hydroxycyclohex-1-ene-1-carboxylate

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Chemical Property of methyl (3S,4R,5R)-5-acetoxy-3-azido-4-hydroxycyclohex-1-ene-1-carboxylate

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Technology Process of methyl (3S,4R,5R)-5-acetoxy-3-azido-4-hydroxycyclohex-1-ene-1-carboxylate

There total 9 articles about methyl (3S,4R,5R)-5-acetoxy-3-azido-4-hydroxycyclohex-1-ene-1-carboxylate 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%

: 352533-27-8
methyl 5-O-acetylshikimate 3,4-cyclic sulfite

: 352533-29-0
methyl (3S,4R,5R)-5-acetoxy-3-azido-4-hydroxycyclohex-1-ene-1-carboxylate

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 20 ℃; for 20h;
DOI:10.1016/S0008-6215(01)00079-9

Reference yield:

: 88165-26-8
methyl 3,4-O-isopropylideneshikimate

: 352533-29-0
methyl (3S,4R,5R)-5-acetoxy-3-azido-4-hydroxycyclohex-1-ene-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: 100 percent / pyridine / 1 h / 20 °C

2: 97 percent / SOCl₂; Et₃N / tetrahydrofuran / 3 h / 20 °C

3: 17 mg / pyridine / 1 h / 20 °C

4: 92 percent / NaN₃ / dimethylformamide / 20 h / 20 °C

With pyridine; thionyl chloride; sodium azide; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(01)00079-9

Reference yield:

: 77-95-2
D-(-)-quinic acid

: 352533-29-0
methyl (3S,4R,5R)-5-acetoxy-3-azido-4-hydroxycyclohex-1-ene-1-carboxylate

Guidance literature:: Multi-step reaction with 9 steps

1: 100 percent / H₂SO₄ / 20 °C

2: 47 percent / pyridine / 2 h / 20 °C

3: 61 percent / SOCl₂ / pyridine / 2 h / 20 °C

4: 92 percent / H₂SO₄ / methanol / 20 °C

5: 92 mg / Dowex-50 (H+) / acetone / 3 h / 20 °C

6: 100 percent / pyridine / 1 h / 20 °C

7: 97 percent / SOCl₂; Et₃N / tetrahydrofuran / 3 h / 20 °C

8: 17 mg / pyridine / 1 h / 20 °C

9: 92 percent / NaN₃ / dimethylformamide / 20 h / 20 °C

With pyridine; thionyl chloride; sodium azide; Dowex-50 (H+); sulfuric acid; triethylamine; In tetrahydrofuran; pyridine; methanol; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0008-6215(01)00079-9