Acetic acid (1aS,8R,9aS)-7-benzyloxy-5-benzyloxymethoxymethyl-8-hydroxymethyl-9-oxo-1-(toluene-4-sulfonyl)-1,1a,2,8,9,9a-hexahydro-1,3-diaza-benzo[a]cyclopropa[e]cycloocten-3-yl ester

Base Information

• Chemical Name: Acetic acid (1aS,8R,9aS)-7-benzyloxy-5-benzyloxymethoxymethyl-8-hydroxymethyl-9-oxo-1-(toluene-4-sulfonyl)-1,1a,2,8,9,9a-hexahydro-1,3-diaza-benzo[a]cyclopropa[e]cycloocten-3-yl ester
• CAS No.: 177958-10-0
• Molecular Formula: C₃₇H₃₈N₂O₉S
• Molecular Weight: 686.783

Synonyms:Acetic acid (1aS,8R,9aS)-7-benzyloxy-5-benzyloxymethoxymethyl-8-hydroxymethyl-9-oxo-1-(toluene-4-sulfonyl)-1,1a,2,8,9,9a-hexahydro-1,3-diaza-benzo[a]cyclopropa[e]cycloocten-3-yl ester

Chemical Property of Acetic acid (1aS,8R,9aS)-7-benzyloxy-5-benzyloxymethoxymethyl-8-hydroxymethyl-9-oxo-1-(toluene-4-sulfonyl)-1,1a,2,8,9,9a-hexahydro-1,3-diaza-benzo[a]cyclopropa[e]cycloocten-3-yl ester

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

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Technology Process of Acetic acid (1aS,8R,9aS)-7-benzyloxy-5-benzyloxymethoxymethyl-8-hydroxymethyl-9-oxo-1-(toluene-4-sulfonyl)-1,1a,2,8,9,9a-hexahydro-1,3-diaza-benzo[a]cyclopropa[e]cycloocten-3-yl ester

There total 21 articles about Acetic acid (1aS,8R,9aS)-7-benzyloxy-5-benzyloxymethoxymethyl-8-hydroxymethyl-9-oxo-1-(toluene-4-sulfonyl)-1,1a,2,8,9,9a-hexahydro-1,3-diaza-benzo[a]cyclopropa[e]cycloocten-3-yl 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: 88.0%

Acetic acid (1aS,8R,9aS)-7-benzyloxy-5-benzyloxymethoxymethyl-8-(tert-butyl-diphenyl-silanyloxymethyl)-9-oxo-1-(toluene-4-sulfonyl)-1,1a,2,8,9,9a-hexahydro-1,3-diaza-benzo[a]cyclopropa[e]cycloocten-3-yl ester (177958-09-7) → Acetic acid (1aS,8R,9aS)-7-benzyloxy-5-benzyloxymethoxymethyl-8-hydroxymethyl-9-oxo-1-(toluene-4-sulfonyl)-1,1a,2,8,9,9a-hexahydro-1,3-diaza-benzo[a]cyclopropa[e]cycloocten-3-yl ester (177958-10-0)

Guidance literature:

With pyridine hydrogenfluoride; In pyridine; at 0 - 25 ℃;

DOI:10.1016/0040-4039(96)00595-3

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → Acetic acid (1aS,8R,9aS)-7-benzyloxy-5-benzyloxymethoxymethyl-8-hydroxymethyl-9-oxo-1-(toluene-4-sulfonyl)-1,1a,2,8,9,9a-hexahydro-1,3-diaza-benzo[a]cyclopropa[e]cycloocten-3-yl ester (177958-10-0)

Guidance literature:

Multi-step reaction with 17 steps

1: Et₃N / dimethylformamide / 4 h / Ambient temperature

2: 94 percent / Et₃N / CH₂Cl₂ / 3 h / Ambient temperature

3: 92 percent / NaH, imidazole / paraffin; tetrahydrofuran / 0.5 h / Heating

4: 99 percent / (HF)n*Py / 0.67 h / -10 °C

5: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / Ambient temperature

6: 1.) LiN(TMS)2, 2.) NaBH₄ / 1.) THF, -78 deg C -> -5 deg C, 3 h, 2.) H₂O, 0 deg C, 20 min

7: 79 percent / Et₃N, DMAP / CH₂Cl₂ / 5 h / Ambient temperature

8: 93 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / Ambient temperature

9: 93 percent / (HF)n*Py / 1 h / Ambient temperature

10: 64 percent / DBU / tetrahydrofuran / 3 h / Ambient temperature

11: 87 percent / NaBH₄ / tetrahydrofuran; H₂O / 1 h / Ambient temperature

12: 71 percent / Et₃N, DMAP / CH₂Cl₂ / 7 h / Ambient temperature

13: 83 percent / Ph₃P, Pd(PPh₃, octanoic acid / tetrahydrofuran / 2 h / Ambient temperature

14: 67 percent / MCPBA / CH₂Cl₂ / 0.5 h / 0 °C

15: 69 percent / NaHCO₃ / 5 h / -5 - 10 °C

16: 88 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.33 h / Ambient temperature

17: 88 percent / (HF)n*Py / 1.) -10 deg C -> room temperature, 2.) room temperature, 2 h

With 1H-imidazole; dmap; sodium tetrahydroborate; Octanoic acid; (HF)n*Py; Pd(PPh₃; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; paraffin;

DOI:10.1016/S0040-4020(97)00652-2

Reference yield:

(2R,3S)-3-[N-allyloxycarbonyl-3-benzyloxy-5-benzyloxymethoxymethyl-2-(2-hydroxyethyl)anilino]methyl-1-p-toluenesulfonyl-2-aziridinemethanol (177958-00-8) → Acetic acid (1aS,8R,9aS)-7-benzyloxy-5-benzyloxymethoxymethyl-8-hydroxymethyl-9-oxo-1-(toluene-4-sulfonyl)-1,1a,2,8,9,9a-hexahydro-1,3-diaza-benzo[a]cyclopropa[e]cycloocten-3-yl ester (177958-10-0)

Guidance literature:

Multi-step reaction with 13 steps

1: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / Ambient temperature

2: 1.) LiN(TMS)2, 2.) NaBH₄ / 1.) THF, -78 deg C -> -5 deg C, 3 h, 2.) H₂O, 0 deg C, 20 min

3: 79 percent / Et₃N, DMAP / CH₂Cl₂ / 5 h / Ambient temperature

4: 93 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / Ambient temperature

5: 93 percent / (HF)n*Py / 1 h / Ambient temperature

6: 64 percent / DBU / tetrahydrofuran / 3 h / Ambient temperature

7: 87 percent / NaBH₄ / tetrahydrofuran; H₂O / 1 h / Ambient temperature

8: 71 percent / Et₃N, DMAP / CH₂Cl₂ / 7 h / Ambient temperature

9: 83 percent / Ph₃P, Pd(PPh₃, octanoic acid / tetrahydrofuran / 2 h / Ambient temperature

10: 67 percent / MCPBA / CH₂Cl₂ / 0.5 h / 0 °C

11: 69 percent / NaHCO₃ / 5 h / -5 - 10 °C

12: 88 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.33 h / Ambient temperature

13: 88 percent / (HF)n*Py / 1.) -10 deg C -> room temperature, 2.) room temperature, 2 h

With dmap; sodium tetrahydroborate; Octanoic acid; (HF)n*Py; Pd(PPh₃; sodium hydrogencarbonate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water;

DOI:10.1016/S0040-4020(97)00652-2

upstream raw materials:

Acetic acid (1aS,8R,9aS)-7-benzyloxy-5-benzyloxymethoxymethyl-8-(tert-butyl-diphenyl-silanyloxymethyl)-9-oxo-1-(toluene-4-sulfonyl)-1,1a,2,8,9,9a-hexahydro-1,3-diaza-benzo[a]cyclopropa[e]cycloocten-3-yl ester

p-toluenesulfonyl chloride

{3-Benzyloxy-5-benzyloxymethoxymethyl-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-phenyl}-carbamic acid allyl ester

(2R,3S)-3-[N-allyloxycarbonyl-3-benzyloxy-5-benzyloxymethoxymethyl-2-(2-hydroxyethyl)anilino]methyl-1-p-toluenesulfonyl-2-aziridinemethanol

Downstream raw materials:

C₃₅H₃₆N₂O₈S

(1aS,3S,8S,9S,9aS)-7-benzyloxy-5-benzyloxymethoxymethyl-1a,2,3,8,9,9a-hexahydro-9-hydroxy-8-hydroxymethyl-1-p-toluenesulfonyl-3,9-epoxy-3H-azirino[2,3-c][1]benzazocine

(1aS,3S,8S,9S,9aS)-9-acetoxy-7-benzyloxy-5-benzyloxymethoxymethyl-8-carbamoyloxymethyl-1,1a,2,8,9,9a-hexahydro-3,9-epoxy-3H-azirino[2,3-c][1]benzazocine

(4aS,9S,10aS,11aS,11bS)-5-benzyloxy-7-benzyloxymethoxymethyl-4,4a,10,10a,11,11a-hexahydro-2-oxo-11-p-toluenesulfonyl-9,11b-epoxyazirino[2,3-c]-1,3-dioxino[4,5-e][1]benzazocine

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