Benzoic acid (2R,4R,6S)-2-((S)-2,3-dimethoxy-propyl)-6-methoxycarbonimidoyl-3,3-dimethyl-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,4R,6S)-2-((S)-2,3-dimethoxy-propyl)-6-methoxycarbonimidoyl-3,3-dimethyl-tetrahydro-pyran-4-yl ester
• CAS No.: 73787-25-4
• Molecular Formula: C₂₁H₃₁NO₆
• Molecular Weight: 393.48
• Mol file: 73787-25-4.mol

Synonyms:

Chemical Property of Benzoic acid (2R,4R,6S)-2-((S)-2,3-dimethoxy-propyl)-6-methoxycarbonimidoyl-3,3-dimethyl-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2R,4R,6S)-2-((S)-2,3-dimethoxy-propyl)-6-methoxycarbonimidoyl-3,3-dimethyl-tetrahydro-pyran-4-yl ester

There total 18 articles about Benzoic acid (2R,4R,6S)-2-((S)-2,3-dimethoxy-propyl)-6-methoxycarbonimidoyl-3,3-dimethyl-tetrahydro-pyran-4-yl ester 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: 100.0%

(+/-)-18-epi-benzoylpedamide (73787-23-2,94536-96-6,103728-87-6,129261-34-3) + trimethoxonium tetrafluoroborate (420-37-1) → Benzoic acid (2R,4R,6S)-2-((S)-2,3-dimethoxy-propyl)-6-methoxycarbonimidoyl-3,3-dimethyl-tetrahydro-pyran-4-yl ester (73787-25-4,85279-96-5,111319-47-2)

Guidance literature:

In dichloromethane; at 20 ℃; for 1h;

DOI:10.1039/c39870000106

Reference yield:

(1,2-Dimethyl-propenyloxy)-dimethyl-phenyl-silane (65335-67-3) → Benzoic acid (2R,4R,6S)-2-((S)-2,3-dimethoxy-propyl)-6-methoxycarbonimidoyl-3,3-dimethyl-tetrahydro-pyran-4-yl ester (73787-25-4,85279-96-5,111319-47-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 91 percent / TiCl₄ / CH₂Cl₂ / 1 h / -70 °C

2: pyridine / toluene / 1 h / 0 °C

3: LDA / hexane; tetrahydrofuran / 1 h / -70 °C

4: 99 percent / K₂CO₃ / acetone / 1) 2 h, reflux, 2) 1 h, RT

5: 70 percent / DIBAL-H / toluene / 3 h / -70 °C

6: BF₃OEt₂ / CH₂Cl₂ / 1.5 h / 0 °C

7: HCl / tetrahydrofuran / 0.5 h / Ambient temperature

8: CeCl₃ heptahydrate, NaBH₄ / methanol / 0.08 h / -78 °C

9: 74 percent / aq. K₂CO₃ solution (30percent), H₂O₂ (30percent) / ethanol / 1.17 h / Ambient temperature

10: CH₂Cl₂ / 6 h / Ambient temperature

With pyridine; hydrogenchloride; sodium tetrahydroborate; cerium(III) chloride; boron trifluoride diethyl etherate; dihydrogen peroxide; titanium tetrachloride; diisobutylaluminium hydride; potassium carbonate; lithium diisopropyl amide; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; acetone; toluene;

DOI:10.1016/S0040-4020(01)81981-5

Reference yield:

C12H21ClO5 (94493-08-0,94493-09-1,139403-52-4,139403-64-8) → Benzoic acid (2R,4R,6S)-2-((S)-2,3-dimethoxy-propyl)-6-methoxycarbonimidoyl-3,3-dimethyl-tetrahydro-pyran-4-yl ester (73787-25-4,85279-96-5,111319-47-2)

Guidance literature:

Multi-step reaction with 8 steps

1: LDA / hexane; tetrahydrofuran / 1 h / -70 °C

2: 99 percent / K₂CO₃ / acetone / 1) 2 h, reflux, 2) 1 h, RT

3: 70 percent / DIBAL-H / toluene / 3 h / -70 °C

4: BF₃OEt₂ / CH₂Cl₂ / 1.5 h / 0 °C

5: HCl / tetrahydrofuran / 0.5 h / Ambient temperature

6: CeCl₃ heptahydrate, NaBH₄ / methanol / 0.08 h / -78 °C

7: 74 percent / aq. K₂CO₃ solution (30percent), H₂O₂ (30percent) / ethanol / 1.17 h / Ambient temperature

8: CH₂Cl₂ / 6 h / Ambient temperature

With hydrogenchloride; sodium tetrahydroborate; cerium(III) chloride; boron trifluoride diethyl etherate; dihydrogen peroxide; diisobutylaluminium hydride; potassium carbonate; lithium diisopropyl amide; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; acetone; toluene;

DOI:10.1016/S0040-4020(01)81981-5

upstream raw materials:

(+/-)-18-epi-benzoylpedamide

trimethoxonium tetrafluoroborate

(1,2-Dimethyl-propenyloxy)-dimethyl-phenyl-silane

C₁₂H₂₁ClO₅

Downstream raw materials:

C₄₅H₅₇NO₁₁Se