methyl (3R,4S,5R)-3-benzoylamino-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-cyclohex-1-en-1-carboxylate

Base Information

Chemical Name:methyl (3R,4S,5R)-3-benzoylamino-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-cyclohex-1-en-1-carboxylate
CAS No.:245054-43-7
Molecular Formula:C₂₁H₂₇NO₇
Molecular Weight:405.448
Hs Code.:

Synonyms:methyl (3R,4S,5R)-3-benzoylamino-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-cyclohex-1-en-1-carboxylate

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Chemical Property of methyl (3R,4S,5R)-3-benzoylamino-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-cyclohex-1-en-1-carboxylate

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Technology Process of methyl (3R,4S,5R)-3-benzoylamino-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-cyclohex-1-en-1-carboxylate

There total 6 articles about methyl (3R,4S,5R)-3-benzoylamino-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-cyclohex-1-en-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: 80.0%

: 98-88-4
benzoyl chloride

: 245054-40-4
methyl (3R,4S,5R)-3-amino-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-cyclohex-1-en-1-carboxylate

: 245054-43-7
methyl (3R,4S,5R)-3-benzoylamino-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-cyclohex-1-en-1-carboxylate

Guidance literature:: With dmap; In pyridine; for 2h; Ambient temperature;
DOI:10.1016/S0040-4020(99)00431-7

Reference yield:

: 176798-26-8
(2S,3S,4aR,6S,8R,8aR)-6,8-Dihydroxy-2,3-dimethoxy-2,3-dimethyl-octahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester

: 245054-43-7
methyl (3R,4S,5R)-3-benzoylamino-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-cyclohex-1-en-1-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: 1) oxalyl chloride, DMSO, 2) diisopropylethylamine / 1) CH₂Cl₂, -60 - -50 deg C, 2) CH₂Cl₂, -60 - -50 deg C to room temperature; room temperature, 30 min

2: 80 percent / diisopropylethylamine, acetic anhydride, 4-(dimethylamino)pyridine / CH₂Cl₂ / Ambient temperature

3: 73 percent / DIBAL-H / tetrahydrofuran / 0.17 h / -78 °C

4: 98 percent / triphenylphosphine, hydrazoic acid, diisopropyl azodicarboxylate / tetrahydrofuran / 1 h / Ambient temperature

5: 73 percent / PPh₃, H₂O / tetrahydrofuran / 4 h / 60 °C

6: 80 percent / DMAP / pyridine / 2 h / Ambient temperature

With dmap; hydrogen azide; oxalyl dichloride; di-isopropyl azodicarboxylate; water; acetic anhydride; diisobutylaluminium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; pyridine; dichloromethane;
DOI:10.1016/S0040-4020(99)00431-7

Reference yield:

: 183474-88-6
methyl (1S,4S,5R)-1-hydroxy-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-3-oxo-cyclohexan-1-carboxylate

: 245054-43-7
methyl (3R,4S,5R)-3-benzoylamino-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-cyclohex-1-en-1-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: 80 percent / diisopropylethylamine, acetic anhydride, 4-(dimethylamino)pyridine / CH₂Cl₂ / Ambient temperature

2: 73 percent / DIBAL-H / tetrahydrofuran / 0.17 h / -78 °C

3: 98 percent / triphenylphosphine, hydrazoic acid, diisopropyl azodicarboxylate / tetrahydrofuran / 1 h / Ambient temperature

4: 73 percent / PPh₃, H₂O / tetrahydrofuran / 4 h / 60 °C

5: 80 percent / DMAP / pyridine / 2 h / Ambient temperature

With dmap; hydrogen azide; di-isopropyl azodicarboxylate; water; acetic anhydride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; pyridine; dichloromethane;
DOI:10.1016/S0040-4020(99)00431-7