(2S,3R)-2-{(2S,3R)-4-Benzyloxy-2-[4-(bis-benzyloxy-phosphoryl)-butyrylamino]-3-hydroxy-butyrylamino}-3-((2R,3S,4R,5S,6S)-3-benzyloxy-4,5-dihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-butyric acid ethyl ester

Base Information

• Chemical Name: (2S,3R)-2-{(2S,3R)-4-Benzyloxy-2-[4-(bis-benzyloxy-phosphoryl)-butyrylamino]-3-hydroxy-butyrylamino}-3-((2R,3S,4R,5S,6S)-3-benzyloxy-4,5-dihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-butyric acid ethyl ester
• CAS No.: 212780-39-7
• Molecular Formula: C₄₈H₆₁N₂O₁₄P
• Molecular Weight: 920.991

Synonyms:(2S,3R)-2-{(2S,3R)-4-Benzyloxy-2-[4-(bis-benzyloxy-phosphoryl)-butyrylamino]-3-hydroxy-butyrylamino}-3-((2R,3S,4R,5S,6S)-3-benzyloxy-4,5-dihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-butyric acid ethyl ester

Chemical Property of (2S,3R)-2-{(2S,3R)-4-Benzyloxy-2-[4-(bis-benzyloxy-phosphoryl)-butyrylamino]-3-hydroxy-butyrylamino}-3-((2R,3S,4R,5S,6S)-3-benzyloxy-4,5-dihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-butyric acid ethyl ester

Chemical Property:

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Technology Process of (2S,3R)-2-{(2S,3R)-4-Benzyloxy-2-[4-(bis-benzyloxy-phosphoryl)-butyrylamino]-3-hydroxy-butyrylamino}-3-((2R,3S,4R,5S,6S)-3-benzyloxy-4,5-dihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-butyric acid ethyl ester

There total 9 articles about (2S,3R)-2-{(2S,3R)-4-Benzyloxy-2-[4-(bis-benzyloxy-phosphoryl)-butyrylamino]-3-hydroxy-butyrylamino}-3-((2R,3S,4R,5S,6S)-3-benzyloxy-4,5-dihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-butyric 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:

6-deoxy-L-galactose (73-34-7,87-96-7,488-79-9,551-63-3,609-01-8,643-17-4,643-18-5,4164-09-4,6014-42-2,6155-36-8,6189-71-5,6696-41-9,6736-43-2,13224-93-6,22611-09-2,28161-49-1,28161-50-4,28161-52-6,45864-36-6,63814-64-2,71116-59-1,71116-61-5,72598-05-1,87936-88-7,87936-89-8,97466-79-0,116908-82-8,120442-60-6,123484-22-0,133576-32-6) → (2S,3R)-2-{(2S,3R)-4-Benzyloxy-2-[4-(bis-benzyloxy-phosphoryl)-butyrylamino]-3-hydroxy-butyrylamino}-3-((2R,3S,4R,5S,6S)-3-benzyloxy-4,5-dihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-butyric acid ethyl ester (212780-39-7)

Guidance literature:

Multi-step reaction with 9 steps

1: pyridine, DMAP / 0 - 20 °C

2: BF₃*Et₂O / 0 - 20 °C

3: NaOMe, MeOH / 20 °C

4: p-TsOH*H₂O / CH₂Cl₂ / 20 °C

5: 84 percent / NaH, TBAI / tetrahydrofuran

6: CuBr₂, TBAI / CH₂Cl₂; dimethylformamide

7: TFA, H₂O / acetic acid

8: p-TsOH / CH₂Cl₂ / 20 °C

With pyridine; methanol; dmap; boron trifluoride diethyl etherate; water; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; trifluoroacetic acid; copper(ll) bromide; In tetrahydrofuran; dichloromethane; acetic acid; N,N-dimethyl-formamide;

DOI:10.1002/(SICI)1521-3773(19980703)37:12<1707::AID-ANIE1707>3.0.CO;2-V

Reference yield:

ethyl 2,3,4-tri-O-acetyl-1-thio-β-L-fucopyranoside (127501-41-1) → (2S,3R)-2-{(2S,3R)-4-Benzyloxy-2-[4-(bis-benzyloxy-phosphoryl)-butyrylamino]-3-hydroxy-butyrylamino}-3-((2R,3S,4R,5S,6S)-3-benzyloxy-4,5-dihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-butyric acid ethyl ester (212780-39-7)

Guidance literature:

Multi-step reaction with 7 steps

1: NaOMe, MeOH / 20 °C

2: p-TsOH*H₂O / CH₂Cl₂ / 20 °C

3: 84 percent / NaH, TBAI / tetrahydrofuran

4: CuBr₂, TBAI / CH₂Cl₂; dimethylformamide

5: TFA, H₂O / acetic acid

6: p-TsOH / CH₂Cl₂ / 20 °C

With methanol; water; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; trifluoroacetic acid; copper(ll) bromide; In tetrahydrofuran; dichloromethane; acetic acid; N,N-dimethyl-formamide;

DOI:10.1002/(SICI)1521-3773(19980703)37:12<1707::AID-ANIE1707>3.0.CO;2-V

Reference yield:

1,2,3,4-tetra-O-acetyl-L-fucopyranose (7404-35-5,17081-04-8,20853-37-6,27821-10-9,27821-11-0,30021-94-4,33947-15-8,34371-40-9,34371-41-0,35521-79-0,36807-81-5,36807-82-6,50615-78-6,51921-33-6,62182-03-0,64913-16-2,70004-81-8,84622-47-9,87303-56-8,108942-32-1,108942-33-2,109430-94-6,143394-72-3,24332-95-4) → (2S,3R)-2-{(2S,3R)-4-Benzyloxy-2-[4-(bis-benzyloxy-phosphoryl)-butyrylamino]-3-hydroxy-butyrylamino}-3-((2R,3S,4R,5S,6S)-3-benzyloxy-4,5-dihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-butyric acid ethyl ester (212780-39-7)

Guidance literature:

Multi-step reaction with 8 steps

1: BF₃*Et₂O / 0 - 20 °C

2: NaOMe, MeOH / 20 °C

3: p-TsOH*H₂O / CH₂Cl₂ / 20 °C

4: 84 percent / NaH, TBAI / tetrahydrofuran

5: CuBr₂, TBAI / CH₂Cl₂; dimethylformamide

6: TFA, H₂O / acetic acid

7: p-TsOH / CH₂Cl₂ / 20 °C

With methanol; boron trifluoride diethyl etherate; water; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; trifluoroacetic acid; copper(ll) bromide; In tetrahydrofuran; dichloromethane; acetic acid; N,N-dimethyl-formamide;

DOI:10.1002/(SICI)1521-3773(19980703)37:12<1707::AID-ANIE1707>3.0.CO;2-V

upstream raw materials:

ethanol

4-(dibenzylphosphonyl)butanoic acid

(2S,3R)-3-[(3aR,4S,6R,7S,7aR)-7-Benzyloxy-2-(4-hydroxymethyl-phenyl)-4-methyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid allyl ester

6-deoxy-L-galactose

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