(4S,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-5-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid 2,2,2-trichloro-ethyl ester

Base Information

• Chemical Name: (4S,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-5-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid 2,2,2-trichloro-ethyl ester
• CAS No.: 193893-14-0
• Molecular Formula: C₃₄H₄₂Cl₃NO₆Si
• Molecular Weight: 695.155

Synonyms:(4S,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-5-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid 2,2,2-trichloro-ethyl ester

Chemical Property of (4S,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-5-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid 2,2,2-trichloro-ethyl ester

Chemical Property:

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Technology Process of (4S,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-5-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid 2,2,2-trichloro-ethyl ester

There total 12 articles about (4S,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-5-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid 2,2,2-trichloro-ethyl 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%

2,2-dimethoxy-propane (77-76-9) + [(1S,2R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-hydroxy-3-(4-methoxy-benzyloxy)-propyl]-carbamic acid 2,2,2-trichloro-ethyl ester (193893-13-9) → (4S,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-5-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid 2,2,2-trichloro-ethyl ester (193893-14-0)

Guidance literature:

With toluene-4-sulfonic acid; In acetone; for 21h; Ambient temperature;

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

Reference yield:

(R)-4-[(R)-1-Benzyloxy-2-(4-methoxy-benzyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolane (193893-08-2) → (4S,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-5-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid 2,2,2-trichloro-ethyl ester (193893-14-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 95 percent / H₂ / Raney Ni / ethanol / 1 h / 760 Torr / Ambient temperature

2: 98 percent / Et₃N / CH₂Cl₂ / 0 °C

3: 97 percent / aq. HCl / methanol / Ambient temperature

4: 85 percent / K₂CO₃ / methanol / 0.5 h / Ambient temperature

5: 53 percent / NaN₃, NH₄Cl / ethanol / 17 h / Heating

6: 93 percent / Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

7: Ph₃P / tetrahydrofuran; H₂O / 17 h / Ambient temperature

8: aq. NaHCO₃ / 0.5 h / Ambient temperature

9: 92 percent / TsOH / acetone / 21 h / Ambient temperature

With hydrogenchloride; dmap; sodium azide; hydrogen; sodium hydrogencarbonate; potassium carbonate; ammonium chloride; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; nickel; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetone;

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

Reference yield:

(2R,3S)-2,3-epoxy-4-O-(4-methoxybenzyl)butan-1,4-diol (143833-82-3) → (4S,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-5-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid 2,2,2-trichloro-ethyl ester (193893-14-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 53 percent / NaN₃, NH₄Cl / ethanol / 17 h / Heating

2: 93 percent / Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

3: Ph₃P / tetrahydrofuran; H₂O / 17 h / Ambient temperature

4: aq. NaHCO₃ / 0.5 h / Ambient temperature

5: 92 percent / TsOH / acetone / 21 h / Ambient temperature

With dmap; sodium azide; sodium hydrogencarbonate; ammonium chloride; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; ethanol; dichloromethane; water; acetone;

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

upstream raw materials:

2,2-dimethoxy-propane

[(1S,2R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-hydroxy-3-(4-methoxy-benzyloxy)-propyl]-carbamic acid 2,2,2-trichloro-ethyl ester

(2R,3S)-2,3-epoxy-4-O-(4-methoxybenzyl)butan-1,4-diol

(Z)-4-(4-methoxybenzyloxy)but-2-en-1-ol

Downstream raw materials:

(4S,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid 2,2,2-trichloro-ethyl ester

(4S,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-5-trifluoromethanesulfonyloxymethyl-oxazolidine-3-carboxylic acid 2,2,2-trichloro-ethyl ester

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