(3aS,4S,6aR)-4-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-carbamoyl-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid benzyl ester

Base Information

• Chemical Name: (3aS,4S,6aR)-4-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-carbamoyl-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid benzyl ester
• CAS No.: 128368-60-5
• Molecular Formula: C₂₄H₃₈N₂O₆Si
• Molecular Weight: 478.661

Synonyms:

Chemical Property of (3aS,4S,6aR)-4-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-carbamoyl-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid benzyl ester

Chemical Property:

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Technology Process of (3aS,4S,6aR)-4-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-carbamoyl-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid benzyl ester

There total 8 articles about (3aS,4S,6aR)-4-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-carbamoyl-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid benzyl 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:

(R)-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]((4R,5R)-2,2-dimethyl-5-{[(methylsulfonyl)oxy]methyl}-1,3-dioxolan-4-yl)methyl methanesulfonate (7115-24-4) → (3aS,4S,6aR)-4-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-carbamoyl-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid benzyl ester (128368-60-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 62 percent / sodium azide / H₂O; dimethylformamide

2: 56 percent / camphorsulphonic acid / methanol; H₂O

3: 95 percent / barium methoxide / methanol

6: 73 percent / hydrogen / palladium on carbon / ethanol

8: hydrogen peroxide, hexene / methanol

With 1-hexene; sodium azide; camphor-10-sulfonic acid; hydrogen; dihydrogen peroxide; barium methoxide; palladium on activated charcoal; In methanol; ethanol; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(01)93953-X

Reference yield:

[(2R,3S)-3-((4R,5R)-5-Azidomethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-oxiranyl]-acetonitrile (128368-55-8) → (3aS,4S,6aR)-4-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-carbamoyl-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid benzyl ester (128368-60-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 73 percent / hydrogen / palladium on carbon / ethanol

3: hydrogen peroxide, hexene / methanol

With 1-hexene; hydrogen; dihydrogen peroxide; palladium on activated charcoal; In methanol; ethanol;

DOI:10.1016/S0040-4039(01)93953-X

Reference yield:

4,5-anhydro-1-azido-1-deoxy-2,3-O-isopropylidene-D-talitol (128442-43-3) → (3aS,4S,6aR)-4-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-carbamoyl-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid benzyl ester (128368-60-5)

Guidance literature:

Multi-step reaction with 6 steps

3: 73 percent / hydrogen / palladium on carbon / ethanol

5: hydrogen peroxide, hexene / methanol

With 1-hexene; hydrogen; dihydrogen peroxide; palladium on activated charcoal; In methanol; ethanol;

DOI:10.1016/S0040-4039(01)93953-X

upstream raw materials:

(3aS,4R,6aR)-4-((R)-2-Carbamoyl-1-hydroxy-ethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid benzyl ester

(R)-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]((4R,5R)-2,2-dimethyl-5-{[(methylsulfonyl)oxy]methyl}-1,3-dioxolan-4-yl)methyl methanesulfonate

(R)-3-((3aS,4R,6aR)-2,2-Dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl)-3-hydroxy-propionitrile

4,5-anhydro-1-azido-1-deoxy-2,3-O-isopropylidene-D-talitol

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