(4S,5S)-5-Dibenzylamino-2-oxo-5-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-4-trimethylsilanyloxy-pentanoic acid ethyl ester

Base Information

• Chemical Name: (4S,5S)-5-Dibenzylamino-2-oxo-5-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-4-trimethylsilanyloxy-pentanoic acid ethyl ester
• CAS No.: 213180-81-5
• Molecular Formula: C₃₄H₄₉NO₈Si
• Molecular Weight: 627.85

Synonyms:

Chemical Property of (4S,5S)-5-Dibenzylamino-2-oxo-5-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-4-trimethylsilanyloxy-pentanoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S)-5-Dibenzylamino-2-oxo-5-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-4-trimethylsilanyloxy-pentanoic acid ethyl ester

There total 10 articles about (4S,5S)-5-Dibenzylamino-2-oxo-5-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-4-trimethylsilanyloxy-pentanoic acid 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:

(2R,3R)-2-Azido-3-benzyloxy-3-((4S,5R)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-propan-1-ol (213180-72-4) → (4S,5S)-5-Dibenzylamino-2-oxo-5-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-4-trimethylsilanyloxy-pentanoic acid ethyl ester (213180-81-5)

Guidance literature:

Multi-step reaction with 9 steps

1: H₂ / 10percent Pd/C / methanol / 16 h / 18 °C / 2585.7 Torr

2: K₂CO₃ / H₂O; acetonitrile / 16 h / 60 °C

3: 62 percent / TFOH / 3 h / 0 °C

4: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 to 0 deg C, 1 h, 2.) CH₂Cl₂

5: 85 percent / Zn, NH₄Cl, H₂O / tetrahydrofuran / 0.75 h / 0 - 18 °C

6: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 to 0 deg C, 1 h, 2.) CH₂Cl₂

7: NaBH₄ / ethanol / 4 h / -10 °C

8: HMDS, pyridine / 19 h / 0 - 18 °C

9: 1.) Ad-mix-α, 2.) Pb(OAc)4, CaCO3 / 1.) t-BuOH, H2O, 18 deg C, 22 h, 2.) CH2Cl2, 18 deg C, 0.33 h

With pyridine; lead(IV) acetate; sodium tetrahydroborate; AD-mix-α; oxalyl dichloride; trifluorormethanesulfonic acid; water; hydrogen; potassium carbonate; ammonium chloride; dimethyl sulfoxide; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; calcium carbonate; zinc; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; water; acetonitrile;

DOI:10.1039/a804524k

Reference yield:

benzyl bromide (100-39-0) → (4S,5S)-5-Dibenzylamino-2-oxo-5-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-4-trimethylsilanyloxy-pentanoic acid ethyl ester (213180-81-5)

Guidance literature:

Multi-step reaction with 8 steps

1: K₂CO₃ / H₂O; acetonitrile / 16 h / 60 °C

2: 62 percent / TFOH / 3 h / 0 °C

3: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 to 0 deg C, 1 h, 2.) CH₂Cl₂

4: 85 percent / Zn, NH₄Cl, H₂O / tetrahydrofuran / 0.75 h / 0 - 18 °C

5: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 to 0 deg C, 1 h, 2.) CH₂Cl₂

6: NaBH₄ / ethanol / 4 h / -10 °C

7: HMDS, pyridine / 19 h / 0 - 18 °C

8: 1.) Ad-mix-α, 2.) Pb(OAc)4, CaCO3 / 1.) t-BuOH, H2O, 18 deg C, 22 h, 2.) CH2Cl2, 18 deg C, 0.33 h

With pyridine; lead(IV) acetate; sodium tetrahydroborate; AD-mix-α; oxalyl dichloride; trifluorormethanesulfonic acid; water; potassium carbonate; ammonium chloride; dimethyl sulfoxide; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; calcium carbonate; zinc; In tetrahydrofuran; ethanol; water; acetonitrile;

DOI:10.1039/a804524k

Reference yield:

(1R,2R)-2-Amino-1-((4S,5R)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-propane-1,3-diol (213180-73-5) → (4S,5S)-5-Dibenzylamino-2-oxo-5-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-4-trimethylsilanyloxy-pentanoic acid ethyl ester (213180-81-5)

Guidance literature:

Multi-step reaction with 8 steps

1: K₂CO₃ / H₂O; acetonitrile / 16 h / 60 °C

2: 62 percent / TFOH / 3 h / 0 °C

3: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 to 0 deg C, 1 h, 2.) CH₂Cl₂

4: 85 percent / Zn, NH₄Cl, H₂O / tetrahydrofuran / 0.75 h / 0 - 18 °C

5: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 to 0 deg C, 1 h, 2.) CH₂Cl₂

6: NaBH₄ / ethanol / 4 h / -10 °C

7: HMDS, pyridine / 19 h / 0 - 18 °C

8: 1.) Ad-mix-α, 2.) Pb(OAc)4, CaCO3 / 1.) t-BuOH, H2O, 18 deg C, 22 h, 2.) CH2Cl2, 18 deg C, 0.33 h

With pyridine; lead(IV) acetate; sodium tetrahydroborate; AD-mix-α; oxalyl dichloride; trifluorormethanesulfonic acid; water; potassium carbonate; ammonium chloride; dimethyl sulfoxide; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; calcium carbonate; zinc; In tetrahydrofuran; ethanol; water; acetonitrile;

DOI:10.1039/a804524k

upstream raw materials:

(4S,5S)-5-Dibenzylamino-2-methylene-5-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-4-trimethylsilanyloxy-pentanoic acid ethyl ester

benzyl bromide

(1R,2R)-2-Amino-1-((4S,5R)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-propane-1,3-diol

(2R,3R)-2-Azido-3-benzyloxy-3-((4S,5R)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-propan-1-ol

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