(2R,3R,6R)-6-(methoxycarbonylmethyl)-3-hydroxy-2-hydroxymethyl-1-phenylsulfonylpiperidine acetonide

Base Information

• Chemical Name: (2R,3R,6R)-6-(methoxycarbonylmethyl)-3-hydroxy-2-hydroxymethyl-1-phenylsulfonylpiperidine acetonide
• CAS No.: 216860-84-3
• Molecular Formula: C₁₈H₂₅NO₆S
• Molecular Weight: 383.466

Synonyms:(2R,3R,6R)-6-(methoxycarbonylmethyl)-3-hydroxy-2-hydroxymethyl-1-phenylsulfonylpiperidine acetonide

Chemical Property of (2R,3R,6R)-6-(methoxycarbonylmethyl)-3-hydroxy-2-hydroxymethyl-1-phenylsulfonylpiperidine acetonide

Chemical Property:

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Technology Process of (2R,3R,6R)-6-(methoxycarbonylmethyl)-3-hydroxy-2-hydroxymethyl-1-phenylsulfonylpiperidine acetonide

There total 10 articles about (2R,3R,6R)-6-(methoxycarbonylmethyl)-3-hydroxy-2-hydroxymethyl-1-phenylsulfonylpiperidine acetonide 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: 75.0%

(4R,5R,E/Z)-5-[(phenylsulfonyl)amino]-4-(4-methoxycarbonyl-3-butenyl)-2,2-dimethyl-1,3-dioxane → (2R,3R,6R)-6-(methoxycarbonylmethyl)-3-hydroxy-2-hydroxymethyl-1-phenylsulfonylpiperidine acetonide (216860-84-3)

Guidance literature:

With sodium hydride; In 1,2-dimethoxyethane; at 50 - 55 ℃; for 60h;

DOI:10.1021/jo980592s

Reference yield: 75.0%

(4R,5R,E)-5-[(phenylsulfonyl)amino]-4-(4-methoxycarbonyl-3-butenyl)-2,2-dimethyl-1,3-dioxane (216860-81-0) → (2R,3R,6R)-6-(methoxycarbonylmethyl)-3-hydroxy-2-hydroxymethyl-1-phenylsulfonylpiperidine acetonide (216860-84-3)

Guidance literature:

With sodium hydride; In 1,2-dimethoxyethane; at 50 - 55 ℃; for 60h;

DOI:10.1021/jo980592s

Reference yield: 68.0%

(4R,5R,Z)-5-[(phenylsulfonyl)amino]-4-(4-methoxycarbonyl-3-butenyl)-2,2-dimethyl-1,3-dioxane (216860-82-1) → (2R,3R,6R)-6-(methoxycarbonylmethyl)-3-hydroxy-2-hydroxymethyl-1-phenylsulfonylpiperidine acetonide (216860-84-3)

Guidance literature:

With sodium hydride; In 1,2-dimethoxyethane; at 20 ℃; for 144h;

DOI:10.1021/jo980592s

upstream raw materials:

(4R,5R,Z)-5-[(phenylsulfonyl)amino]-4-(4-methoxycarbonyl-3-butenyl)-2,2-dimethyl-1,3-dioxane

(4R,5R,E)-5-[(phenylsulfonyl)amino]-4-(4-methoxycarbonyl-3-butenyl)-2,2-dimethyl-1,3-dioxane

benzenesulfonyl chloride

N-(Phenylsulfonyl)-D-serine

Downstream raw materials:

(2R,3R,6R)-6-methoxycarbonylmethyl-3-tert-butyldimethylsilyloxy-2-tert-butyldimethylsilyloxymethyl-1-phenylsulfonylpiperidine

(2R,3R,6R,7R)-3-tert-butyldimethylsilyloxy-2-(p-nitrobenzyloxycarbonyl)-7-ethyl-8-oxo-1-azabicyclo[4.2.0]octane

(2S,3R,6R,7R)-2-(p-nitrobenzyloxycarbonyl)-7-ethyl-8-oxo-3-hydroxy-1-azabicyclo[4.2.0]octane

(6R,7R)-7-Ethyl-3-hydroxy-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester

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