(S)-2-((S)-2-{[(1S,3S,4S,5S)-3-(tert-Butoxycarbonylamino-methyl)-4-hydroxy-2,6-dioxa-bicyclo[3.2.0]heptane-1-carbonyl]-amino}-3-phenyl-propionylamino)-4-methyl-pentanoic acid methyl ester

Base Information

Chemical Name:(S)-2-((S)-2-{[(1S,3S,4S,5S)-3-(tert-Butoxycarbonylamino-methyl)-4-hydroxy-2,6-dioxa-bicyclo[3.2.0]heptane-1-carbonyl]-amino}-3-phenyl-propionylamino)-4-methyl-pentanoic acid methyl ester
CAS No.:561018-12-0
Molecular Formula:C₂₈H₄₁N₃O₉
Molecular Weight:563.648
Hs Code.:

(S)-2-((S)-2-{[(1S,3S,4S,5S)-3-(tert-Butoxycarbonylamino-methyl)-4-hydroxy-2,6-dioxa-bicyclo[3.2.0]heptane-1-carbonyl]-amino}-3-phenyl-propionylamino)-4-methyl-pentanoic acid methyl ester

Synonyms:(S)-2-((S)-2-{[(1S,3S,4S,5S)-3-(tert-Butoxycarbonylamino-methyl)-4-hydroxy-2,6-dioxa-bicyclo[3.2.0]heptane-1-carbonyl]-amino}-3-phenyl-propionylamino)-4-methyl-pentanoic acid methyl ester

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Chemical Property of (S)-2-((S)-2-{[(1S,3S,4S,5S)-3-(tert-Butoxycarbonylamino-methyl)-4-hydroxy-2,6-dioxa-bicyclo[3.2.0]heptane-1-carbonyl]-amino}-3-phenyl-propionylamino)-4-methyl-pentanoic acid methyl ester

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Technology Process of (S)-2-((S)-2-{[(1S,3S,4S,5S)-3-(tert-Butoxycarbonylamino-methyl)-4-hydroxy-2,6-dioxa-bicyclo[3.2.0]heptane-1-carbonyl]-amino}-3-phenyl-propionylamino)-4-methyl-pentanoic acid methyl ester

There total 15 articles about (S)-2-((S)-2-{[(1S,3S,4S,5S)-3-(tert-Butoxycarbonylamino-methyl)-4-hydroxy-2,6-dioxa-bicyclo[3.2.0]heptane-1-carbonyl]-amino}-3-phenyl-propionylamino)-4-methyl-pentanoic acid methyl 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: 45.0%

: 64152-76-7
methyl (S)-2-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanamido)-4-methylpentanoate

: 561017-85-4
2,5-anhydro-6-tert-butoxycarbonylamino-6-deoxy-2-C,3-O-methylene-L-allo-hexonic acid

: 561018-12-0
(S)-2-((S)-2-{[(1S,3S,4S,5S)-3-(tert-Butoxycarbonylamino-methyl)-4-hydroxy-2,6-dioxa-bicyclo[3.2.0]heptane-1-carbonyl]-amino}-3-phenyl-propionylamino)-4-methyl-pentanoic acid methyl ester

Guidance literature:: methyl (S)-2-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanamido)-4-methylpentanoate; With trifluoroacetic acid; In dichloromethane; for 0.0833333h;

2,5-anhydro-6-tert-butoxycarbonylamino-6-deoxy-2-C,3-O-methylene-L-allo-hexonic acid; With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 0 ℃; for 16h;
DOI:10.1016/S0040-4020(03)00288-6

Reference yield:

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

: 561018-12-0
(S)-2-((S)-2-{[(1S,3S,4S,5S)-3-(tert-Butoxycarbonylamino-methyl)-4-hydroxy-2,6-dioxa-bicyclo[3.2.0]heptane-1-carbonyl]-amino}-3-phenyl-propionylamino)-4-methyl-pentanoic acid methyl ester

Guidance literature:: Multi-step reaction with 15 steps

1.1: 75 percent / Co₂(CO)8 / CH₂Cl₂ / 16 h / 30 °C

2.1: 95 percent / AcOH / H₂O; tetrahydrofuran / 2 h / 20 °C

3.1: 93 percent / pyridine / 16 h / 20 °C

4.1: 96 percent / NaN₃ / dimethylformamide / 1.5 h / 75 °C

5.1: 100 percent / t-BuOK / methanol / 2 h / 20 °C

6.1: 2.08 g / p-TsOH / acetone / 3 h / 20 °C

7.1: Dess-Martin periodinate / CH₂Cl₂ / 1 h / 0 °C

8.1: 2N aq. NaOH / H₂O; dioxane / 1 h / 0 °C

8.2: 0.51 g / NaBH₄ / H₂O; dioxane / 2 h / 0 °C

9.1: 92 percent / pyridine / 16 h / 20 °C

10.1: 89 percent / 4M aq. HCl / tetrahydrofuran / 2 h / 20 °C

11.1: 89 percent / 1M NaOH / H₂O; dioxane / 1 h / 25 °C

12.1: 0.074 g / 1M NaOH / H₂O; dioxane / 96 h / 85 °C

13.1: 70 percent / Me₃P / tetrahydrofuran; toluene / 5 h / -20 °C

14.1: 70 percent / TEMPO; KBr; NaHCO₃ / NaOCl / H₂O / 4 h / 0 °C

15.1: TFA / CH₂Cl₂ / 0.08 h

15.2: 45 percent / HOBt; EDC*HCl; NMM / dimethylformamide / 16 h / 0 °C

With hydrogenchloride; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hydroxide; sodium azide; dicobalt octacarbonyl; potassium tert-butylate; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; trifluoroacetic acid; potassium bromide; trimethylphosphane; sodium hypochlorite; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; 8.2: Cannizaro reduction / 13.1: Staudinger reaction;
DOI:10.1016/S0040-4020(03)00288-6

Reference yield:

: 58632-95-4
2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

: 561018-12-0
(S)-2-((S)-2-{[(1S,3S,4S,5S)-3-(tert-Butoxycarbonylamino-methyl)-4-hydroxy-2,6-dioxa-bicyclo[3.2.0]heptane-1-carbonyl]-amino}-3-phenyl-propionylamino)-4-methyl-pentanoic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 70 percent / Me₃P / tetrahydrofuran; toluene / 5 h / -20 °C

2.1: 70 percent / TEMPO; KBr; NaHCO₃ / NaOCl / H₂O / 4 h / 0 °C

3.1: TFA / CH₂Cl₂ / 0.08 h

3.2: 45 percent / HOBt; EDC*HCl; NMM / dimethylformamide / 16 h / 0 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hydrogencarbonate; trifluoroacetic acid; potassium bromide; trimethylphosphane; sodium hypochlorite; In tetrahydrofuran; dichloromethane; water; toluene; 1.1: Staudinger reaction;
DOI:10.1016/S0040-4020(03)00288-6