(S)-2-Amino-3-[3-benzyloxy-4-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-phenyl]-propionic acid

Base Information

• Chemical Name: (S)-2-Amino-3-[3-benzyloxy-4-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-phenyl]-propionic acid
• CAS No.: 1054643-80-9
• Molecular Formula: C₅₁H₅₃NO₈
• Molecular Weight: 807.984
• Mol file: 1054643-80-9.mol

Synonyms:

Chemical Property of (S)-2-Amino-3-[3-benzyloxy-4-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-phenyl]-propionic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-Amino-3-[3-benzyloxy-4-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-phenyl]-propionic acid

There total 13 articles about (S)-2-Amino-3-[3-benzyloxy-4-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-phenyl]-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:

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one (13096-62-3) → (S)-2-Amino-3-[3-benzyloxy-4-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-phenyl]-propionic acid (1054643-80-9)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 91 percent / tetrahydrofuran / 2 h / -78 °C

2.1: 78 percent / Et₃SiH; BF₃*OEt₂ / CH₂Cl₂ / 12 h / -78 °C

3.1: ozone / CH₂Cl₂; methanol / -78 °C

3.2: PPh₃

4.1: 22.9 g / toluene / 2 h / Heating

5.1: 88 percent / DIBAL / toluene / -78 - 25 °C

6.1: MnO₂ / CH₂Cl₂ / 3 h / Heating

7.1: 13.3 g / CH₂Cl₂ / 3 h / Heating

8.1: 65 percent / ethyl chloroformate; Et₃N / tetrahydrofuran / 0.5 h / 20 °C

9.1: 87 percent / K₂CO₃ / acetone / 12 h

10.1: 91 percent / LiAlH₄ / tetrahydrofuran / 1 h / 20 °C

11.1: 79 percent / NBS; PPh₃ / tetrahydrofuran / 2 h / 20 °C

12.1: NaH / dimethylformamide / 0.33 h

12.2: 65 percent / dimethylformamide / 2 h / 20 °C

13.1: NaOH / ethanol / 5 h / Heating

13.2: Aspergillus species Acylase I; aq. NaOH / propan-2-ol / 48 h / 20 °C / pH 7.8

With triethylsilane; manganese(IV) oxide; sodium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; boron trifluoride diethyl etherate; chloroformic acid ethyl ester; sodium hydride; diisobutylaluminium hydride; potassium carbonate; ozone; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 4.1: Wittig reaction / 7.1: Wittig reaction;

DOI:10.1002/1521-3765(20020415)8:8<1872::AID-CHEM1872>3.0.CO;2-A

Reference yield:

2,3,4,6-tetra-O-benzyl-D-glucopyranose (6564-72-3) → (S)-2-Amino-3-[3-benzyloxy-4-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-phenyl]-propionic acid (1054643-80-9)

Guidance literature:

Multi-step reaction with 14 steps

1.1: Jones reagent / acetone

2.1: 91 percent / tetrahydrofuran / 2 h / -78 °C

3.1: 78 percent / Et₃SiH; BF₃*OEt₂ / CH₂Cl₂ / 12 h / -78 °C

4.1: ozone / CH₂Cl₂; methanol / -78 °C

4.2: PPh₃

5.1: 22.9 g / toluene / 2 h / Heating

6.1: 88 percent / DIBAL / toluene / -78 - 25 °C

7.1: MnO₂ / CH₂Cl₂ / 3 h / Heating

8.1: 13.3 g / CH₂Cl₂ / 3 h / Heating

9.1: 65 percent / ethyl chloroformate; Et₃N / tetrahydrofuran / 0.5 h / 20 °C

10.1: 87 percent / K₂CO₃ / acetone / 12 h

11.1: 91 percent / LiAlH₄ / tetrahydrofuran / 1 h / 20 °C

12.1: 79 percent / NBS; PPh₃ / tetrahydrofuran / 2 h / 20 °C

13.1: NaH / dimethylformamide / 0.33 h

13.2: 65 percent / dimethylformamide / 2 h / 20 °C

14.1: NaOH / ethanol / 5 h / Heating

14.2: Aspergillus species Acylase I; aq. NaOH / propan-2-ol / 48 h / 20 °C / pH 7.8

With triethylsilane; manganese(IV) oxide; sodium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; jones reagent; boron trifluoride diethyl etherate; chloroformic acid ethyl ester; sodium hydride; diisobutylaluminium hydride; potassium carbonate; ozone; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 5.1: Wittig reaction / 8.1: Wittig reaction;

DOI:10.1002/1521-3765(20020415)8:8<1872::AID-CHEM1872>3.0.CO;2-A

Reference yield:

(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanal (96689-97-3,120520-77-6,120520-79-8,120520-80-1,120520-78-7) → (S)-2-Amino-3-[3-benzyloxy-4-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-phenyl]-propionic acid (1054643-80-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 22.9 g / toluene / 2 h / Heating

2.1: 88 percent / DIBAL / toluene / -78 - 25 °C

3.1: MnO₂ / CH₂Cl₂ / 3 h / Heating

4.1: 13.3 g / CH₂Cl₂ / 3 h / Heating

5.1: 65 percent / ethyl chloroformate; Et₃N / tetrahydrofuran / 0.5 h / 20 °C

6.1: 87 percent / K₂CO₃ / acetone / 12 h

7.1: 91 percent / LiAlH₄ / tetrahydrofuran / 1 h / 20 °C

8.1: 79 percent / NBS; PPh₃ / tetrahydrofuran / 2 h / 20 °C

9.1: NaH / dimethylformamide / 0.33 h

9.2: 65 percent / dimethylformamide / 2 h / 20 °C

10.1: NaOH / ethanol / 5 h / Heating

10.2: Aspergillus species Acylase I; aq. NaOH / propan-2-ol / 48 h / 20 °C / pH 7.8

With manganese(IV) oxide; sodium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; chloroformic acid ethyl ester; sodium hydride; diisobutylaluminium hydride; potassium carbonate; triethylamine; triphenylphosphine; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 1.1: Wittig reaction / 4.1: Wittig reaction;

DOI:10.1002/1521-3765(20020415)8:8<1872::AID-CHEM1872>3.0.CO;2-A

upstream raw materials:

2-acetamido-2-[3-benzyloxy-4-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-ylmethyl)benzyl]malonic diethyl ester

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

2,3,4,6-tetra-O-benzyl-D-glucopyranose

(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanal