(S)-3-{2-[(2R,3R,4S,5S)-5-Benzyloxy-4-(tert-butoxycarbonyl-methyl-amino)-3-hydroxy-tetrahydro-pyran-2-ylmethyl]-oxiranyl}-2-tert-butoxycarbonylamino-propionic acid methyl ester

Base Information

Chemical Name:(S)-3-{2-[(2R,3R,4S,5S)-5-Benzyloxy-4-(tert-butoxycarbonyl-methyl-amino)-3-hydroxy-tetrahydro-pyran-2-ylmethyl]-oxiranyl}-2-tert-butoxycarbonylamino-propionic acid methyl ester
CAS No.:289505-52-8
Molecular Formula:C₃₀H₄₆N₂O₁₀
Molecular Weight:594.703
Hs Code.:

(S)-3-{2-[(2R,3R,4S,5S)-5-Benzyloxy-4-(tert-butoxycarbonyl-methyl-amino)-3-hydroxy-tetrahydro-pyran-2-ylmethyl]-oxiranyl}-2-tert-butoxycarbonylamino-propionic acid methyl ester

Synonyms:(S)-3-{2-[(2R,3R,4S,5S)-5-Benzyloxy-4-(tert-butoxycarbonyl-methyl-amino)-3-hydroxy-tetrahydro-pyran-2-ylmethyl]-oxiranyl}-2-tert-butoxycarbonylamino-propionic acid methyl ester

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Chemical Property of (S)-3-{2-[(2R,3R,4S,5S)-5-Benzyloxy-4-(tert-butoxycarbonyl-methyl-amino)-3-hydroxy-tetrahydro-pyran-2-ylmethyl]-oxiranyl}-2-tert-butoxycarbonylamino-propionic acid methyl ester

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Technology Process of (S)-3-{2-[(2R,3R,4S,5S)-5-Benzyloxy-4-(tert-butoxycarbonyl-methyl-amino)-3-hydroxy-tetrahydro-pyran-2-ylmethyl]-oxiranyl}-2-tert-butoxycarbonylamino-propionic acid methyl ester

There total 21 articles about (S)-3-{2-[(2R,3R,4S,5S)-5-Benzyloxy-4-(tert-butoxycarbonyl-methyl-amino)-3-hydroxy-tetrahydro-pyran-2-ylmethyl]-oxiranyl}-2-tert-butoxycarbonylamino-propionic 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: 92.0%

: 289505-43-7
(S)-4-[(2R,3R,4S,5S)-5-Benzyloxy-4-(tert-butoxycarbonyl-methyl-amino)-3-hydroxy-tetrahydro-pyran-2-ylmethyl]-2-tert-butoxycarbonylamino-pent-4-enoic acid methyl ester

: 289505-52-8
(S)-3-{2-[(2R,3R,4S,5S)-5-Benzyloxy-4-(tert-butoxycarbonyl-methyl-amino)-3-hydroxy-tetrahydro-pyran-2-ylmethyl]-oxiranyl}-2-tert-butoxycarbonylamino-propionic acid methyl ester

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In phosphate buffer; dichloromethane; at 20 ℃; pH=7.0;
DOI:10.1016/S0040-4039(00)00518-9

Reference yield:

: 100-39-0
benzyl bromide

: 289505-52-8
(S)-3-{2-[(2R,3R,4S,5S)-5-Benzyloxy-4-(tert-butoxycarbonyl-methyl-amino)-3-hydroxy-tetrahydro-pyran-2-ylmethyl]-oxiranyl}-2-tert-butoxycarbonylamino-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 21 steps

1.1: 86 percent / NaH / dimethylformamide / 0 - 20 °C

2.1: NaN₃; NH₄Cl / H₂O; 2-methoxy-ethanol / Heating

3.1: BF₃*Et₂O / 20 °C

4.1: 78 percent / Et₃SiH; TMSOTF; BF₃*OEt₂ / CH₂Cl₂; acetonitrile / 20 °C

5.1: NaOMe / methanol / 20 °C

6.1: 2,6-lutidine / CH₂Cl₂

7.1: PPh₃ / tetrahydrofuran / 20 °C

7.2: H₂O / 45 °C

8.1: Et₃N / CH₂Cl₂

9.1: 96 percent / NaH / dimethylformamide / 0 °C

10.1: 99 percent / camphorsulfonic acid / CH₂Cl₂; methanol / 20 °C

11.1: 2,6-lutidine / CH₂Cl₂ / -78 °C

12.1: BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C

13.1: Bu₄NF / tetrahydrofuran / 20 °C

14.1: (COCl)2; DMSO; i-Pr₂NEt / CH₂Cl₂ / -78 - 20 °C

15.1: NaBH₄ / tetrahydrofuran; methanol / -78 - 0 °C

16.1: 2,6-lutidine / CH₂Cl₂ / 0 °C

17.1: B-iodo-9-BBN / pentane / -20 °C

17.2: AcOH / pentane

18.1: PdCl₂(PPh₃)2 / tetrahydrofuran; N,N-dimethyl-acetamide / 35 °C

19.1: Bu₄NF / tetrahydrofuran / 20 °C

20.1: Et₃N / CH₂Cl₂ / 20 °C

21.1: 92 percent / m-chloroperbenzoic acid / CH₂Cl₂; aq. phosphate buffer / 20 °C / pH 7.0

With 2,6-dimethylpyridine; triethylsilane; sodium tetrahydroborate; n-butyllithium; sodium azide; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium methylate; sodium hydride; ammonium chloride; dimethyl sulfoxide; B-iodo-9-BBN; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; phosphate buffer; dichloromethane; 2-methoxy-ethanol; N,N-dimethyl acetamide; water; N,N-dimethyl-formamide; acetonitrile; pentane; 1.1: Etherification / 2.1: Ring cleavage / 3.1: Acetylation / 4.1: Reduction / 5.1: Deacetylation / 6.1: Etherification / 7.1: Reduction / 7.2: Hydrolysis / 8.1: Esterification / 9.1: Methylation / 10.1: Hydrolysis / 11.1: Esterification / 12.1: Substitution / 13.1: Hydrolysis / 14.1: Oxidation / 15.1: Reduction / 16.1: Etherification / 17.1: Iodination / 17.2: Hydrolysis / 18.1: Substitution / 19.1: Hydrolysis / 20.1: Esterification / 21.1: Oxidation;
DOI:10.1016/S0040-4039(00)00518-9

Reference yield:

: 213594-43-5
1,6:3,4-dianhydro-2-O-benzyl-β-D-altropyranose

: 289505-52-8
(S)-3-{2-[(2R,3R,4S,5S)-5-Benzyloxy-4-(tert-butoxycarbonyl-methyl-amino)-3-hydroxy-tetrahydro-pyran-2-ylmethyl]-oxiranyl}-2-tert-butoxycarbonylamino-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 20 steps

1.1: NaN₃; NH₄Cl / H₂O; 2-methoxy-ethanol / Heating

2.1: BF₃*Et₂O / 20 °C

3.1: 78 percent / Et₃SiH; TMSOTF; BF₃*OEt₂ / CH₂Cl₂; acetonitrile / 20 °C

4.1: NaOMe / methanol / 20 °C

5.1: 2,6-lutidine / CH₂Cl₂

6.1: PPh₃ / tetrahydrofuran / 20 °C

6.2: H₂O / 45 °C

7.1: Et₃N / CH₂Cl₂

8.1: 96 percent / NaH / dimethylformamide / 0 °C

9.1: 99 percent / camphorsulfonic acid / CH₂Cl₂; methanol / 20 °C

10.1: 2,6-lutidine / CH₂Cl₂ / -78 °C

11.1: BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C

12.1: Bu₄NF / tetrahydrofuran / 20 °C

13.1: (COCl)2; DMSO; i-Pr₂NEt / CH₂Cl₂ / -78 - 20 °C

14.1: NaBH₄ / tetrahydrofuran; methanol / -78 - 0 °C

15.1: 2,6-lutidine / CH₂Cl₂ / 0 °C

16.1: B-iodo-9-BBN / pentane / -20 °C

16.2: AcOH / pentane

17.1: PdCl₂(PPh₃)2 / tetrahydrofuran; N,N-dimethyl-acetamide / 35 °C

18.1: Bu₄NF / tetrahydrofuran / 20 °C

19.1: Et₃N / CH₂Cl₂ / 20 °C

20.1: 92 percent / m-chloroperbenzoic acid / CH₂Cl₂; aq. phosphate buffer / 20 °C / pH 7.0

With 2,6-dimethylpyridine; triethylsilane; sodium tetrahydroborate; n-butyllithium; sodium azide; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium methylate; sodium hydride; ammonium chloride; dimethyl sulfoxide; B-iodo-9-BBN; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; phosphate buffer; dichloromethane; 2-methoxy-ethanol; N,N-dimethyl acetamide; water; N,N-dimethyl-formamide; acetonitrile; pentane; 1.1: Ring cleavage / 2.1: Acetylation / 3.1: Reduction / 4.1: Deacetylation / 5.1: Etherification / 6.1: Reduction / 6.2: Hydrolysis / 7.1: Esterification / 8.1: Methylation / 9.1: Hydrolysis / 10.1: Esterification / 11.1: Substitution / 12.1: Hydrolysis / 13.1: Oxidation / 14.1: Reduction / 15.1: Etherification / 16.1: Iodination / 16.2: Hydrolysis / 17.1: Substitution / 18.1: Hydrolysis / 19.1: Esterification / 20.1: Oxidation;
DOI:10.1016/S0040-4039(00)00518-9