(2S,3R,6R)-6-[(R)-5-(2,2-Dimethyl-propionyloxy)-4-hydroxy-pent-1-ynyl]-2-methyl-3-triisopropylsilanyloxy-piperidine-1-carboxylic acid benzyl ester

Base Information

Chemical Name:(2S,3R,6R)-6-[(R)-5-(2,2-Dimethyl-propionyloxy)-4-hydroxy-pent-1-ynyl]-2-methyl-3-triisopropylsilanyloxy-piperidine-1-carboxylic acid benzyl ester
CAS No.:191592-77-5
Molecular Formula:C₃₃H₅₃NO₆Si
Molecular Weight:587.872
Hs Code.:

(2S,3R,6R)-6-[(R)-5-(2,2-Dimethyl-propionyloxy)-4-hydroxy-pent-1-ynyl]-2-methyl-3-triisopropylsilanyloxy-piperidine-1-carboxylic acid benzyl ester

Synonyms:(2S,3R,6R)-6-[(R)-5-(2,2-Dimethyl-propionyloxy)-4-hydroxy-pent-1-ynyl]-2-methyl-3-triisopropylsilanyloxy-piperidine-1-carboxylic acid benzyl ester

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Chemical Property of (2S,3R,6R)-6-[(R)-5-(2,2-Dimethyl-propionyloxy)-4-hydroxy-pent-1-ynyl]-2-methyl-3-triisopropylsilanyloxy-piperidine-1-carboxylic acid benzyl ester

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Technology Process of (2S,3R,6R)-6-[(R)-5-(2,2-Dimethyl-propionyloxy)-4-hydroxy-pent-1-ynyl]-2-methyl-3-triisopropylsilanyloxy-piperidine-1-carboxylic acid benzyl ester

There total 11 articles about (2S,3R,6R)-6-[(R)-5-(2,2-Dimethyl-propionyloxy)-4-hydroxy-pent-1-ynyl]-2-methyl-3-triisopropylsilanyloxy-piperidine-1-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: 52.0%

: 191592-81-1
(2S,3R)-6-[(R)-5-(2,2-Dimethyl-propionyloxy)-4-hydroxy-pent-1-ynyl]-2-methyl-3-triisopropylsilanyloxy-3,4-dihydro-2H-pyridine-1-carboxylic acid benzyl ester

: (2S,3R,6R)-6-[(R)-5-(2,2-Dimethyl-propionyloxy)-4-hydroxy-pent-1-ynyl]-3-hydroxy-2-methyl-piperidine-1-carboxylic acid benzyl ester

: 191592-77-5
(2S,3R,6R)-6-[(R)-5-(2,2-Dimethyl-propionyloxy)-4-hydroxy-pent-1-ynyl]-2-methyl-3-triisopropylsilanyloxy-piperidine-1-carboxylic acid benzyl ester

Guidance literature:: With sodium cyanoborohydride; trifluoroacetic acid; at -50 - -40 ℃;
DOI:10.1021/jo970788c

Reference yield:

: 130609-14-2
(R)-5-((R)-1-hydroxyethyl)dihydrofuran-2(3H)-one

: 191592-77-5
(2S,3R,6R)-6-[(R)-5-(2,2-Dimethyl-propionyloxy)-4-hydroxy-pent-1-ynyl]-2-methyl-3-triisopropylsilanyloxy-piperidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) MsCl, 2.) NaN₃, 3.) H₂ / 3.) Pd/C

2: 2.) n-BuLi

3: 88 percent / LiHMDS

4: 88 percent / Pd(PPh₃)4, CuI, Et₃N

5: 52 percent / NaBH₃CN, TFA / -50 - -40 °C

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; sodium azide; hydrogen; sodium cyanoborohydride; methanesulfonyl chloride; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane; palladium on activated charcoal;
DOI:10.1021/jo970788c

Reference yield:

: 143289-01-4
(4R,5R,E)-ethyl 4,5-dihydroxyhex-2-enoate

: 191592-77-5
(2S,3R,6R)-6-[(R)-5-(2,2-Dimethyl-propionyloxy)-4-hydroxy-pent-1-ynyl]-2-methyl-3-triisopropylsilanyloxy-piperidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 92 percent / H₂ / Rh-Al₂O₃

2: 1.) MsCl, 2.) NaN₃, 3.) H₂ / 3.) Pd/C

3: 2.) n-BuLi

4: 88 percent / LiHMDS

5: 88 percent / Pd(PPh₃)4, CuI, Et₃N

6: 52 percent / NaBH₃CN, TFA / -50 - -40 °C

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; sodium azide; hydrogen; sodium cyanoborohydride; methanesulfonyl chloride; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane; palladium on activated charcoal; rhodium on alumina;
DOI:10.1021/jo970788c