Carbonic acid (S)-4-[(4S,5S,6R)-5-(3,4-dimethoxy-benzyloxy)-6-(2,6-dioxo-piperidin-4-yl)-[1,3]dioxan-4-yl]-4-hydroxy-2-methylene-butyl ester 2,2,2-trichloro-ethyl ester

Base Information

• Chemical Name: Carbonic acid (S)-4-[(4S,5S,6R)-5-(3,4-dimethoxy-benzyloxy)-6-(2,6-dioxo-piperidin-4-yl)-[1,3]dioxan-4-yl]-4-hydroxy-2-methylene-butyl ester 2,2,2-trichloro-ethyl ester
• CAS No.: 113425-65-3
• Molecular Formula: C₂₆H₃₂Cl₃NO₁₁
• Molecular Weight: 640.899

Synonyms:Carbonic acid (S)-4-[(4S,5S,6R)-5-(3,4-dimethoxy-benzyloxy)-6-(2,6-dioxo-piperidin-4-yl)-[1,3]dioxan-4-yl]-4-hydroxy-2-methylene-butyl ester 2,2,2-trichloro-ethyl ester

Chemical Property of Carbonic acid (S)-4-[(4S,5S,6R)-5-(3,4-dimethoxy-benzyloxy)-6-(2,6-dioxo-piperidin-4-yl)-[1,3]dioxan-4-yl]-4-hydroxy-2-methylene-butyl ester 2,2,2-trichloro-ethyl ester

Chemical Property:

Purity/Quality:

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Technology Process of Carbonic acid (S)-4-[(4S,5S,6R)-5-(3,4-dimethoxy-benzyloxy)-6-(2,6-dioxo-piperidin-4-yl)-[1,3]dioxan-4-yl]-4-hydroxy-2-methylene-butyl ester 2,2,2-trichloro-ethyl ester

There total 9 articles about Carbonic acid (S)-4-[(4S,5S,6R)-5-(3,4-dimethoxy-benzyloxy)-6-(2,6-dioxo-piperidin-4-yl)-[1,3]dioxan-4-yl]-4-hydroxy-2-methylene-butyl ester 2,2,2-trichloro-ethyl 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: 58.4%

Carbonic acid 2,2,2-trichloro-ethyl ester 2-trimethylsilanylmethyl-allyl ester (96625-53-5) + (4R,5S,6R)-5-(3,4-Dimethoxy-benzyloxy)-6-(2,6-dioxo-piperidin-4-yl)-[1,3]dioxane-4-carbaldehyde (104777-87-9) → Carbonic acid (S)-4-[(4S,5S,6R)-5-(3,4-dimethoxy-benzyloxy)-6-(2,6-dioxo-piperidin-4-yl)-[1,3]dioxan-4-yl]-4-hydroxy-2-methylene-butyl ester 2,2,2-trichloro-ethyl ester (113425-65-3)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 4h;

DOI:10.1016/S0040-4020(01)81662-8

Reference yield:

4-((4R,5S,6S)-5-Hydroxy-6-hydroxymethyl-[1,3]dioxan-4-yl)-piperidine-2,6-dione (102487-45-6,102518-68-3,112419-11-1) → Carbonic acid (S)-4-[(4S,5S,6R)-5-(3,4-dimethoxy-benzyloxy)-6-(2,6-dioxo-piperidin-4-yl)-[1,3]dioxan-4-yl]-4-hydroxy-2-methylene-butyl ester 2,2,2-trichloro-ethyl ester (113425-65-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 98.7 percent / p. TsOH monohydrate / toluene / 5 h / Heating; azeotropic removal of water

2: 64.5 percent / diethylaluminium chloride, triethylsilane / toluene; CH₂Cl₂ / 1.5 h / -60 - -55 °C

3: 64.5 percent / CrO₃, pyridine, acetic anhydride / CH₂Cl₂; dimethylformamide / 0.13 h / Ambient temperature

4: 58.4 percent / BF₃ etherate / CH₂Cl₂ / 4 h / -78 °C

With pyridine; chromium(VI) oxide; triethylsilane; boron trifluoride diethyl etherate; diethylaluminium chloride; acetic anhydride; toluene-4-sulfonic acid; In dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4020(01)81662-8

Reference yield:

(4R,4aS,8aS)-4-(Tetrahydro-[1,3]dioxino[5,4-d][1,3]dioxin-4-yl)-piperidine-2,6-dione (93125-65-6) → Carbonic acid (S)-4-[(4S,5S,6R)-5-(3,4-dimethoxy-benzyloxy)-6-(2,6-dioxo-piperidin-4-yl)-[1,3]dioxan-4-yl]-4-hydroxy-2-methylene-butyl ester 2,2,2-trichloro-ethyl ester (113425-65-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 91.5 percent / acetic acid, sulfuric acid / 2 h / 0 °C

2: 86 percent / sodium, abs. methanol / CHCl₃ / 1.5 h / -18 - -10 °C

3: 98.7 percent / p. TsOH monohydrate / toluene / 5 h / Heating; azeotropic removal of water

4: 64.5 percent / diethylaluminium chloride, triethylsilane / toluene; CH₂Cl₂ / 1.5 h / -60 - -55 °C

5: 64.5 percent / CrO₃, pyridine, acetic anhydride / CH₂Cl₂; dimethylformamide / 0.13 h / Ambient temperature

6: 58.4 percent / BF₃ etherate / CH₂Cl₂ / 4 h / -78 °C

With pyridine; chromium(VI) oxide; methanol; triethylsilane; sulfuric acid; boron trifluoride diethyl etherate; sodium; diethylaluminium chloride; acetic anhydride; toluene-4-sulfonic acid; acetic acid; In dichloromethane; chloroform; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4020(01)81662-8

upstream raw materials:

Carbonic acid 2,2,2-trichloro-ethyl ester 2-trimethylsilanylmethyl-allyl ester

(4R,5S,6R)-5-(3,4-Dimethoxy-benzyloxy)-6-(2,6-dioxo-piperidin-4-yl)-[1,3]dioxane-4-carbaldehyde

4-((4R,5S,6S)-5-Hydroxy-6-hydroxymethyl-[1,3]dioxan-4-yl)-piperidine-2,6-dione

(4R,4aS,8aS)-4-(Tetrahydro-[1,3]dioxino[5,4-d][1,3]dioxin-4-yl)-piperidine-2,6-dione

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