(2S,5S,7S)-7-((R)-1-Phenylcarbamoyl-ethyl)-1,6-dioxa-spiro[4.5]decane-2-carboxylic acid methoxy-methyl-amide

Base Information

• Chemical Name: (2S,5S,7S)-7-((R)-1-Phenylcarbamoyl-ethyl)-1,6-dioxa-spiro[4.5]decane-2-carboxylic acid methoxy-methyl-amide
• CAS No.: 499992-12-0
• Molecular Formula: C₂₀H₂₈N₂O₅
• Molecular Weight: 376.453

Synonyms:(2S,5S,7S)-7-((R)-1-Phenylcarbamoyl-ethyl)-1,6-dioxa-spiro[4.5]decane-2-carboxylic acid methoxy-methyl-amide

Chemical Property of (2S,5S,7S)-7-((R)-1-Phenylcarbamoyl-ethyl)-1,6-dioxa-spiro[4.5]decane-2-carboxylic acid methoxy-methyl-amide

Chemical Property:

Purity/Quality:

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Technology Process of (2S,5S,7S)-7-((R)-1-Phenylcarbamoyl-ethyl)-1,6-dioxa-spiro[4.5]decane-2-carboxylic acid methoxy-methyl-amide

There total 6 articles about (2S,5S,7S)-7-((R)-1-Phenylcarbamoyl-ethyl)-1,6-dioxa-spiro[4.5]decane-2-carboxylic acid methoxy-methyl-amide 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: 91.0%

N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) + (2S,7S)-7-((R)-1-Phenylcarbamoyl-ethyl)-1,6-dioxa-spiro[4.5]decane-2-carboxylic acid ethyl ester → (2S,5S,7S)-7-((R)-1-Phenylcarbamoyl-ethyl)-1,6-dioxa-spiro[4.5]decane-2-carboxylic acid methoxy-methyl-amide (499992-12-0)

Guidance literature:

With isopropylmagnesium chloride; In tetrahydrofuran; at -78 - -20 ℃;

DOI:10.1002/1521-3773(20021202)41:23<4569::AID-ANIE4569>3.0.CO;2-V

Reference yield:

(R)-2-((S)-6-Methoxy-tetrahydro-pyran-2-yl)-N-phenyl-propionamide (499992-08-4) → (2S,5S,7S)-7-((R)-1-Phenylcarbamoyl-ethyl)-1,6-dioxa-spiro[4.5]decane-2-carboxylic acid methoxy-methyl-amide (499992-12-0)

Guidance literature:

Multi-step reaction with 4 steps

1: acetonitrile / 60 °C

2: n-butyllithium / tetrahydrofuran / -78 °C

3: camphorsulfonic acid / methanol; CH₂Cl₂

4: 91 percent / i-PrMgCl / tetrahydrofuran / -78 - -20 °C

With n-butyllithium; camphor-10-sulfonic acid; isopropylmagnesium chloride; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; 2: Wittig coupling;

DOI:10.1002/1521-3773(20021202)41:23<4569::AID-ANIE4569>3.0.CO;2-V

Reference yield:

(2R,3S)-3-Hydroxy-2-methyl-oct-7-enoic acid phenylamide (499992-07-3) → (2S,5S,7S)-7-((R)-1-Phenylcarbamoyl-ethyl)-1,6-dioxa-spiro[4.5]decane-2-carboxylic acid methoxy-methyl-amide (499992-12-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: O₃ / methanol

1.2: dimethylsulfide / methanol / -78 °C

1.3: 96 percent / camphorsulfonic acid

2.1: acetonitrile / 60 °C

3.1: n-butyllithium / tetrahydrofuran / -78 °C

4.1: camphorsulfonic acid / methanol; CH₂Cl₂

5.1: 91 percent / i-PrMgCl / tetrahydrofuran / -78 - -20 °C

With n-butyllithium; camphor-10-sulfonic acid; isopropylmagnesium chloride; ozone; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; 3.1: Wittig coupling;

DOI:10.1002/1521-3773(20021202)41:23<4569::AID-ANIE4569>3.0.CO;2-V

upstream raw materials:

N,O-dimethylhydroxylamine*hydrochloride

(R)-2-((S)-6-Methoxy-tetrahydro-pyran-2-yl)-N-phenyl-propionamide

(2R,3S)-3-Hydroxy-2-methyl-oct-7-enoic acid phenylamide

Downstream raw materials:

(R)-2-((2S,5S,7S)-2-{(S)-[(2R,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-furan-2-yl]-hydroxy-methyl}-1,6-dioxa-spiro[4.5]dec-7-yl)-N-phenyl-propionamide

(R)-2-((2S,5S,7S)-2-{(S)-[(2S,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2-hydroxymethyl-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-hydroxy-methyl}-1,6-dioxa-spiro[4.5]dec-7-yl)-N-phenyl-propionamide

(R)-2-{(2S,5S,7S)-2-[(1R,4R,5R)-6-(tert-Butyl-dimethyl-silanyloxy)-1,5-dihydroxy-4-(4-methoxy-benzyloxy)-2-methylene-hexyl]-1,6-dioxa-spiro[4.5]dec-7-yl}-N-phenyl-propionamide

(R)-2-((2S,5S,7S)-2-{(S)-(tert-Butoxy-diphenyl-silanyloxy)-[(2R,4R,5R)-5-hydroxymethyl-4-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-furan-2-yl]-methyl}-1,6-dioxa-spiro[4.5]dec-7-yl)-N-phenyl-propionamide

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