(3S,4R,5R)-methyl 3-azido-4-hydroxy-5-(methoxymethoxy)cyclohex-1-enecarboxylate

Base Information

Chemical Name:(3S,4R,5R)-methyl 3-azido-4-hydroxy-5-(methoxymethoxy)cyclohex-1-enecarboxylate
CAS No.:1376576-27-0
Molecular Formula:C₁₀H₁₅N₃O₅
Molecular Weight:257.246
Hs Code.:

Synonyms:(3S,4R,5R)-methyl 3-azido-4-hydroxy-5-(methoxymethoxy)cyclohex-1-enecarboxylate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3S,4R,5R)-methyl 3-azido-4-hydroxy-5-(methoxymethoxy)cyclohex-1-enecarboxylate

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Technology Process of (3S,4R,5R)-methyl 3-azido-4-hydroxy-5-(methoxymethoxy)cyclohex-1-enecarboxylate

There total 7 articles about (3S,4R,5R)-methyl 3-azido-4-hydroxy-5-(methoxymethoxy)cyclohex-1-enecarboxylate 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: 83.0%

: 1376575-69-7
(1R,5R,6S)-methyl 5-(methoxymethoxy)-7-oxabicyclo[4.1.0]hept-2-ene-3-carboxylate

: 1376576-27-0
(3S,4R,5R)-methyl 3-azido-4-hydroxy-5-(methoxymethoxy)cyclohex-1-enecarboxylate

Guidance literature:: With sodium azide; ammonium chloride; In ethanol; water; N,N-dimethyl-formamide; at 0 - 25 ℃; for 10h;
DOI:10.1039/c2ob25635e

Reference yield:

: 1376576-24-7
(4R)-methyl 4-(methoxymethoxy)-2-methylene-4-((2S,3R)-3-vinyloxiran-2-yl)butanoate

: 1376576-27-0
(3S,4R,5R)-methyl 3-azido-4-hydroxy-5-(methoxymethoxy)cyclohex-1-enecarboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 14 h / Reflux

2: sodium azide; ammonium chloride / ethanol; water; N,N-dimethyl-formamide / 10 h / 0 - 25 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; sodium azide; ammonium chloride; In ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1039/c2ob25635e

Reference yield:

: 1376576-21-4
(R)-methyl 4-((2S,3R)-3-ethynyloxiran-2-yl)-4-(methoxymethoxy)-2-methylenebutanoate

: 1376576-27-0
(3S,4R,5R)-methyl 3-azido-4-hydroxy-5-(methoxymethoxy)cyclohex-1-enecarboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: pyridine / oct-1-ene; ethyl acetate / 6 h / 25 °C

2: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 14 h / Reflux

3: sodium azide; ammonium chloride / ethanol; water; N,N-dimethyl-formamide / 10 h / 0 - 25 °C

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; sodium azide; ammonium chloride; In ethanol; dichloromethane; oct-1-ene; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1039/c2ob25635e