(S)-2-((2R,3R,5S)-3-Benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-3-(4-methoxy-benzyloxy)-2-(2,2,2-trichloro-acetylamino)-propionic acid

Base Information

• Chemical Name: (S)-2-((2R,3R,5S)-3-Benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-3-(4-methoxy-benzyloxy)-2-(2,2,2-trichloro-acetylamino)-propionic acid
• CAS No.: 475291-27-1
• Molecular Formula: C₂₅H₂₈Cl₃NO₈
• Molecular Weight: 576.858
• Mol file: 475291-27-1.mol

Synonyms:

Chemical Property of (S)-2-((2R,3R,5S)-3-Benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-3-(4-methoxy-benzyloxy)-2-(2,2,2-trichloro-acetylamino)-propionic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-((2R,3R,5S)-3-Benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-3-(4-methoxy-benzyloxy)-2-(2,2,2-trichloro-acetylamino)-propionic acid

There total 12 articles about (S)-2-((2R,3R,5S)-3-Benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-3-(4-methoxy-benzyloxy)-2-(2,2,2-trichloro-acetylamino)-propionic acid 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:

N-{(S)-1-[(2R,3R,5S)-3-benzyloxy-5-methoxyoxolan-2-yl]-1-formyl-2-(4-methoxybenzyloxy)ethyl}trichloroacetamide (475291-26-0) → (S)-2-((2R,3R,5S)-3-Benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-3-(4-methoxy-benzyloxy)-2-(2,2,2-trichloro-acetylamino)-propionic acid (475291-27-1)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; amidosulfuric acid fluoride; In water; tert-butyl alcohol; at 25 ℃; for 0.25h;

DOI:10.1246/bcsj.75.1927

Reference yield:

2,3,5,6-di-O-isopropylidene-D-mannofuranose (7757-38-2,14131-84-1,23262-78-4,27108-13-0,33823-04-0,34685-42-2,57819-52-0,78039-08-4,78039-12-0,78964-16-6,94842-76-9,149342-31-4) → (S)-2-((2R,3R,5S)-3-Benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-3-(4-methoxy-benzyloxy)-2-(2,2,2-trichloro-acetylamino)-propionic acid (475291-27-1)

Guidance literature:

Multi-step reaction with 13 steps

1.1: CCl₄; (Me₂N)3P / tetrahydrofuran / -78 - 0 °C

2.1: Li; liquid ammonia / 0.5 h / -78 °C

3.1: 97 percent / NaH; tetra-n-butylammonium iodide / tetrahydrofuran / 0 - 25 °C

4.1: Hg(OAc)2; water / tetrahydrofuran / 0.5 h / 25 °C

4.2: potassium iodide / tetrahydrofuran; H₂O / 0.25 h / 0 °C

4.3: NaBH₄ / tetrahydrofuran; H₂O / 1.5 h / 0 °C

5.1: 91 percent / acetic acid; water / 14 h / 25 °C

6.1: 69 percent / AcCl / 20 h / 0 °C

7.1: dibutyltin oxide / toluene / 2 h / Heating

7.2: 96 percent / CsF / dimethylformamide / 40 h / 80 °C

8.1: 100 percent / (COCl)2; dimethylsulfoxide; triethylamine / CH₂Cl₂ / 3.5 h / -78 - 0 °C

9.1: 90 percent / LiBr; DBU / acetonitrile / 12 h / -45 °C

10.1: 93 percent / DIBAL-H; DBU / toluene / 0.25 h / -78 °C

11.1: DBU / CH₂Cl₂ / 0.5 h / 0 °C

12.1: K₂CO₃ / xylene / 60 h / 140 °C

12.2: ozone / methanol / 0.25 h / -78 °C

12.3: 486 mg / Me₂S / methanol / -78 - 0 °C

13.1: NaH₂PO₄*2H₂O; HOSO₂NH₂; NaClO₂ / H₂O; 2-methyl-propan-2-ol / 0.25 h / 25 °C

With tetrachloromethane; sodium chlorite; sodium dihydrogenphosphate; oxalyl dichloride; amidosulfuric acid fluoride; mercury(II) diacetate; ammonia; water; tetra-(n-butyl)ammonium iodide; lithium; sodium hydride; diisobutylaluminium hydride; di(n-butyl)tin oxide; potassium carbonate; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; acetyl chloride; lithium bromide; Hexamethylphosphorous triamide; In tetrahydrofuran; dichloromethane; water; toluene; acetonitrile; xylene; tert-butyl alcohol; 8.1: Swern oxidation / 12.1: Overman rearrangement;

DOI:10.1246/bcsj.75.1927

Reference yield:

benzyl bromide (100-39-0) → (S)-2-((2R,3R,5S)-3-Benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-3-(4-methoxy-benzyloxy)-2-(2,2,2-trichloro-acetylamino)-propionic acid (475291-27-1)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 97 percent / NaH; tetra-n-butylammonium iodide / tetrahydrofuran / 0 - 25 °C

2.1: Hg(OAc)2; water / tetrahydrofuran / 0.5 h / 25 °C

2.2: potassium iodide / tetrahydrofuran; H₂O / 0.25 h / 0 °C

2.3: NaBH₄ / tetrahydrofuran; H₂O / 1.5 h / 0 °C

3.1: 91 percent / acetic acid; water / 14 h / 25 °C

4.1: 69 percent / AcCl / 20 h / 0 °C

5.1: dibutyltin oxide / toluene / 2 h / Heating

5.2: 96 percent / CsF / dimethylformamide / 40 h / 80 °C

6.1: 100 percent / (COCl)2; dimethylsulfoxide; triethylamine / CH₂Cl₂ / 3.5 h / -78 - 0 °C

7.1: 90 percent / LiBr; DBU / acetonitrile / 12 h / -45 °C

8.1: 93 percent / DIBAL-H; DBU / toluene / 0.25 h / -78 °C

9.1: DBU / CH₂Cl₂ / 0.5 h / 0 °C

10.1: K₂CO₃ / xylene / 60 h / 140 °C

10.2: ozone / methanol / 0.25 h / -78 °C

10.3: 486 mg / Me₂S / methanol / -78 - 0 °C

11.1: NaH₂PO₄*2H₂O; HOSO₂NH₂; NaClO₂ / H₂O; 2-methyl-propan-2-ol / 0.25 h / 25 °C

With sodium chlorite; sodium dihydrogenphosphate; oxalyl dichloride; amidosulfuric acid fluoride; mercury(II) diacetate; water; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; di(n-butyl)tin oxide; potassium carbonate; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; acetyl chloride; lithium bromide; In tetrahydrofuran; dichloromethane; water; toluene; acetonitrile; xylene; tert-butyl alcohol; 6.1: Swern oxidation / 10.1: Overman rearrangement;

DOI:10.1246/bcsj.75.1927

upstream raw materials:

N-{(S)-1-[(2R,3R,5S)-3-benzyloxy-5-methoxyoxolan-2-yl]-1-formyl-2-(4-methoxybenzyloxy)ethyl}trichloroacetamide

2,3,5,6-di-O-isopropylidene-D-mannofuranose

benzyl bromide

(R)-4-((2S,3R)-3-(benzyloxy)-2,3-dihydrofuran-2-yl)-2,2-dimethyl-1,3-dioxolan

Downstream raw materials:

1-ethyl 8-methyl (E,5R,6R,7S)-5-benzyloxy-6-hydroxy-7-(4-methoxybenzyloxymethyl)-7-(trichloroacetamido)oct-2-enedioate

methyl (E,2S,3R,4R)-4-benzyloxy-3,8-dihydroxy-2-(4-methoxybenzyloxymethyl)-2-(trichloroacetamido)oct-6-enoate

(4S,5R)-5-((E)-(R)-1-Benzyloxy-5-methanesulfonyloxy-pent-3-enyl)-4-(4-methoxy-benzyloxymethyl)-2-oxo-oxazolidine-4-carboxylic acid methyl ester

methyl (4S,5R)-5-[(E,R)-1-benzyloxy-5-hydroxypent-3-en-1-yl]-4-(4-methoxybenzyloxymethyl)-2-oxooxazolidine-4-carboxylate