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

Base Information

• Chemical Name: {3-Benzyloxy-5-benzyloxymethoxymethyl-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-phenyl}-carbamic acid allyl ester
• CAS No.: 177957-70-9
• Molecular Formula: C₃₄H₄₅NO₆Si
• Molecular Weight: 591.82

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

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

Chemical Property:

Purity/Quality:

Safty Information:

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

There total 16 articles about {3-Benzyloxy-5-benzyloxymethoxymethyl-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-phenyl}-carbamic acid allyl 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: 98.0%

3-Benzyloxy-5-benzyloxymethoxymethyl-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-phenylamine (177957-83-4) + Allyl chloroformate (2937-50-0) → {3-Benzyloxy-5-benzyloxymethoxymethyl-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-phenyl}-carbamic acid allyl ester (177957-70-9)

Guidance literature:

With sodium hydrogencarbonate; In dichloromethane; Ambient temperature;

DOI:10.1016/0040-4039(96)00594-1

Reference yield:

5-Hydroxyisophthalic acid (618-83-7) → {3-Benzyloxy-5-benzyloxymethoxymethyl-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-phenyl}-carbamic acid allyl ester (177957-70-9)

Guidance literature:

Multi-step reaction with 16 steps

1: 100 percent / SOCl₂ / 1.5 h / Heating

2: 98 percent / K₂CO₃ / acetone / 3 h / Heating

3: 88 percent / various solvent(s) / 5 h / Heating

4: 99 percent / K₂CO₃ / acetone / 3 h / Heating

5: 95 percent / 4 M NaOH / tetrahydrofuran / 5 h / Heating

6: 72 percent / Br₂, aq. NaHCO₃ / CHCl₃ / 0.08 h / 0 °C

7: Et₃N / tetrahydrofuran / 0.33 h / 0 °C

8: NaBH₄ / H₂O / 0.67 h / 0 °C

9: 85 percent / i-Pr₂EtN / CH₂Cl₂ / 8 h / Ambient temperature

10: 93 percent / Zn, NH₄Cl / ethanol; H₂O / 1 h / 40 °C

11: 76 percent / DPPA, Et₃N, molecular sieves / 1.) room temperature, 1.5 h, 2.) reflux, 5 h

12: 73 percent / OsO₄, NaIO₄ / dioxane; H₂O / 13 h / Ambient temperature

13: 100 percent / NaBH₄ / ethanol / 0.67 h / Ambient temperature

14: 97 percent / Et₃N, DMAP / CH₂Cl₂ / 2 h / Ambient temperature

15: 1.) TBDMSOTf, Py, 2.) TBAF / 1.) CH₂Cl₂, room temperature, 4 h, 2.) THF, room temperature, 1 h

16: 98 percent / aq. NaHCO₃ / CH₂Cl₂ / 13 h / Ambient temperature

With pyridine; dmap; sodium hydroxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; thionyl chloride; molecular sieve; t-butyldimethylsiyl triflate; diphenyl-phosphinic acid; tetrabutyl ammonium fluoride; bromine; sodium hydrogencarbonate; potassium carbonate; ammonium chloride; triethylamine; N-ethyl-N,N-diisopropylamine; zinc; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; chloroform; water; acetone;

DOI:10.1016/S0040-4020(97)00651-0

Reference yield:

Dimethyl 5-hydroxyisophthalate (13036-02-7) → {3-Benzyloxy-5-benzyloxymethoxymethyl-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-phenyl}-carbamic acid allyl ester (177957-70-9)

Guidance literature:

Multi-step reaction with 15 steps

1: 98 percent / K₂CO₃ / acetone / 3 h / Heating

2: 88 percent / various solvent(s) / 5 h / Heating

3: 99 percent / K₂CO₃ / acetone / 3 h / Heating

4: 95 percent / 4 M NaOH / tetrahydrofuran / 5 h / Heating

5: 72 percent / Br₂, aq. NaHCO₃ / CHCl₃ / 0.08 h / 0 °C

6: Et₃N / tetrahydrofuran / 0.33 h / 0 °C

7: NaBH₄ / H₂O / 0.67 h / 0 °C

8: 85 percent / i-Pr₂EtN / CH₂Cl₂ / 8 h / Ambient temperature

9: 93 percent / Zn, NH₄Cl / ethanol; H₂O / 1 h / 40 °C

10: 76 percent / DPPA, Et₃N, molecular sieves / 1.) room temperature, 1.5 h, 2.) reflux, 5 h

11: 73 percent / OsO₄, NaIO₄ / dioxane; H₂O / 13 h / Ambient temperature

12: 100 percent / NaBH₄ / ethanol / 0.67 h / Ambient temperature

13: 97 percent / Et₃N, DMAP / CH₂Cl₂ / 2 h / Ambient temperature

14: 1.) TBDMSOTf, Py, 2.) TBAF / 1.) CH₂Cl₂, room temperature, 4 h, 2.) THF, room temperature, 1 h

15: 98 percent / aq. NaHCO₃ / CH₂Cl₂ / 13 h / Ambient temperature

With pyridine; dmap; sodium hydroxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; molecular sieve; t-butyldimethylsiyl triflate; diphenyl-phosphinic acid; tetrabutyl ammonium fluoride; bromine; sodium hydrogencarbonate; potassium carbonate; ammonium chloride; triethylamine; N-ethyl-N,N-diisopropylamine; zinc; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; chloroform; water; acetone;

DOI:10.1016/S0040-4020(97)00651-0

upstream raw materials:

3-Benzyloxy-5-benzyloxymethoxymethyl-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-phenylamine

Allyl chloroformate

Dimethyl 5-hydroxyisophthalate

5-Hydroxyisophthalic acid

Downstream raw materials:

(4S,5S)-5-[(Allyloxycarbonyl-{3-benzyloxy-5-benzyloxymethoxymethyl-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-phenyl}-amino)-methyl]-4-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid 2,2,2-trichloro-ethyl ester

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

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

[3-Benzyloxy-5-benzyloxymethoxymethyl-2-(2-oxo-ethyl)-phenyl]-[(2S,3S)-3-formyl-1-(toluene-4-sulfonyl)-aziridin-2-ylmethyl]-carbamic acid allyl ester

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