(2S,3S)-3-[(3R,4S)-4-(Benzyloxycarbonyl-methyl-amino)-3-methoxymethoxy-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-benzyloxycarbonyl-2-methyl-propyl ester

Base Information

Chemical Name:(2S,3S)-3-[(3R,4S)-4-(Benzyloxycarbonyl-methyl-amino)-3-methoxymethoxy-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-benzyloxycarbonyl-2-methyl-propyl ester
CAS No.:182822-93-1
Molecular Formula:C₄₅H₆₁NO₁₀
Molecular Weight:775.98
Hs Code.:

(2S,3S)-3-[(3R,4S)-4-(Benzyloxycarbonyl-methyl-amino)-3-methoxymethoxy-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-benzyloxycarbonyl-2-methyl-propyl ester

Synonyms:(2S,3S)-3-[(3R,4S)-4-(Benzyloxycarbonyl-methyl-amino)-3-methoxymethoxy-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-benzyloxycarbonyl-2-methyl-propyl ester

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Chemical Property of (2S,3S)-3-[(3R,4S)-4-(Benzyloxycarbonyl-methyl-amino)-3-methoxymethoxy-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-benzyloxycarbonyl-2-methyl-propyl ester

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Technology Process of (2S,3S)-3-[(3R,4S)-4-(Benzyloxycarbonyl-methyl-amino)-3-methoxymethoxy-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-benzyloxycarbonyl-2-methyl-propyl ester

There total 15 articles about (2S,3S)-3-[(3R,4S)-4-(Benzyloxycarbonyl-methyl-amino)-3-methoxymethoxy-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-benzyloxycarbonyl-2-methyl-propyl 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:

: 112271-08-6
(4S)-40<(tertibutyloxycarbonyl)amino>-3-oxo-5-phenylpentanoic acid ethyl ester

: 182822-93-1
(2S,3S)-3-[(3R,4S)-4-(Benzyloxycarbonyl-methyl-amino)-3-methoxymethoxy-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-benzyloxycarbonyl-2-methyl-propyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 74 percent / NaBH₄ / ethanol / 2 h / -78 °C

2: 77 percent / p-TsOH / H₂O; toluene / 20 h / Heating

3: 81 percent / TFA, NaBH₃CN / CH₂Cl₂ / 1 h / 0 °C

4: 1.74 g / NaHCO₃ / H₂O; acetone / 16 h / Ambient temperature

5: 87 percent / DIPEA / CH₂Cl₂ / 48 h / Ambient temperature

6: 90 percent / K₂CO₃ / methanol / 3 h / Heating

7: 1.) 2,4,6-trichlorobenzoyl chloride, Et₃N, 2.) Et₃N / 1.) THF, rt, 20 min, 2.) THF, rt, 3 h

With sodium tetrahydroborate; 2,4,6-trichlorobenzoyl chloride; sodium cyanoborohydride; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In methanol; ethanol; dichloromethane; water; acetone; toluene;
DOI:10.1016/S0968-0896(98)00208-9

Reference yield:

: 72155-47-6
N-(tert-butoxycarbonyl)-4(S)-amino-3(R)-hydroxy-5-phenylpentanoic acid ethyl ester

: 182822-93-1
(2S,3S)-3-[(3R,4S)-4-(Benzyloxycarbonyl-methyl-amino)-3-methoxymethoxy-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-benzyloxycarbonyl-2-methyl-propyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 77 percent / p-TsOH / H₂O; toluene / 20 h / Heating

2: 81 percent / TFA, NaBH₃CN / CH₂Cl₂ / 1 h / 0 °C

3: 1.74 g / NaHCO₃ / H₂O; acetone / 16 h / Ambient temperature

4: 87 percent / DIPEA / CH₂Cl₂ / 48 h / Ambient temperature

5: 90 percent / K₂CO₃ / methanol / 3 h / Heating

6: 1.) 2,4,6-trichlorobenzoyl chloride, Et₃N, 2.) Et₃N / 1.) THF, rt, 20 min, 2.) THF, rt, 3 h

With 2,4,6-trichlorobenzoyl chloride; sodium cyanoborohydride; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In methanol; dichloromethane; water; acetone; toluene;
DOI:10.1016/S0968-0896(98)00208-9

Reference yield:

: 182621-43-8
(4S,5R)-(4-benzyl-3-(tert-butoxycarbonyl)oxazolidin-5-yl)acetic acid ethyl ester

: 182822-93-1
(2S,3S)-3-[(3R,4S)-4-(Benzyloxycarbonyl-methyl-amino)-3-methoxymethoxy-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-benzyloxycarbonyl-2-methyl-propyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 81 percent / TFA, NaBH₃CN / CH₂Cl₂ / 1 h / 0 °C

2: 1.74 g / NaHCO₃ / H₂O; acetone / 16 h / Ambient temperature

3: 87 percent / DIPEA / CH₂Cl₂ / 48 h / Ambient temperature

4: 90 percent / K₂CO₃ / methanol / 3 h / Heating

5: 1.) 2,4,6-trichlorobenzoyl chloride, Et₃N, 2.) Et₃N / 1.) THF, rt, 20 min, 2.) THF, rt, 3 h

With 2,4,6-trichlorobenzoyl chloride; sodium cyanoborohydride; sodium hydrogencarbonate; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In methanol; dichloromethane; water; acetone;
DOI:10.1016/S0968-0896(98)00208-9