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

Base Information

• Chemical Name: methyl (3R,4S,5R)-3-benzoyloxy-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-cyclohex-1-en-1-carboxylate
• CAS No.: 245054-33-5
• Molecular Formula: C₂₁H₂₆O₈
• Molecular Weight: 406.433
• Mol file: 245054-33-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (3R,4S,5R)-3-benzoyloxy-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-benzoyloxy-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: 99.0%

benzoic acid (65-85-0,8013-63-6) + (2S,3S,4aR,8S,8aR)-methyl 8-hydroxy-2,3-dimethoxy-2,3-dimethyl-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxine-6-carboxylate (245054-31-3) → methyl (3R,4S,5R)-3-benzoyloxy-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-cyclohex-1-en-1-carboxylate (245054-33-5)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; for 1h;

DOI:10.1016/S0040-4020(99)00431-7

Reference yield: 94.0%

benzoyl chloride (98-88-4) + methyl (3R,4S,5R)-3-hydroxy-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-cyclohex-1-en-1-carboxylate (245054-32-4) → methyl (3R,4S,5R)-3-benzoyloxy-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-cyclohex-1-en-1-carboxylate (245054-33-5)

Guidance literature:

With dmap; In pyridine; Ambient temperature;

DOI:10.1016/S0040-4020(99)00431-7

Reference yield:

(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 (176798-26-8) → methyl (3R,4S,5R)-3-benzoyloxy-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-cyclohex-1-en-1-carboxylate (245054-33-5)

Guidance literature:

Multi-step reaction with 4 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: 75 percent / L-Selectride / tetrahydrofuran / 0.17 h / -78 °C

4: 94 percent / DMAP / pyridine / Ambient temperature

With dmap; oxalyl dichloride; acetic anhydride; L-Selectride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; pyridine; dichloromethane;

DOI:10.1016/S0040-4020(99)00431-7

upstream raw materials:

benzoyl chloride

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

benzoic acid

(2S,3S,4aR,8S,8aR)-methyl 8-hydroxy-2,3-dimethoxy-2,3-dimethyl-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxine-6-carboxylate

Downstream raw materials:

methyl shikimate

methyl (3R,4S,5R)-3-benzoyloxy-4,5-dihydroxy-cyclohex-1-en-1-carboxylate