(2S,3R)-3-((2R,3S,4R,5S,6S)-3-Benzyloxy-4,5-dihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid allyl ester

Base Information

• Chemical Name: (2S,3R)-3-((2R,3S,4R,5S,6S)-3-Benzyloxy-4,5-dihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid allyl ester
• CAS No.: 212780-30-8
• Molecular Formula: C₃₅H₃₉NO₉
• Molecular Weight: 617.696

Synonyms:(2S,3R)-3-((2R,3S,4R,5S,6S)-3-Benzyloxy-4,5-dihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid allyl ester

Chemical Property of (2S,3R)-3-((2R,3S,4R,5S,6S)-3-Benzyloxy-4,5-dihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid allyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-3-((2R,3S,4R,5S,6S)-3-Benzyloxy-4,5-dihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid allyl ester

There total 7 articles about (2S,3R)-3-((2R,3S,4R,5S,6S)-3-Benzyloxy-4,5-dihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid allyl 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:

(2S,3R)-3-((3aR,4S,6R,7S,7aR)-7-Benzyloxy-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid allyl ester (289634-87-3) → (2S,3R)-3-((2R,3S,4R,5S,6S)-3-Benzyloxy-4,5-dihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid allyl ester (212780-30-8)

Guidance literature:

With water; trifluoroacetic acid; In acetic acid; Yield given;

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

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)-3-((2R,3S,4R,5S,6S)-3-Benzyloxy-4,5-dihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid allyl ester (212780-30-8)

Guidance literature:

Multi-step reaction with 7 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

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)-3-((2R,3S,4R,5S,6S)-3-Benzyloxy-4,5-dihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid allyl ester (212780-30-8)

Guidance literature:

Multi-step reaction with 5 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

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

upstream raw materials:

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

6-deoxy-L-galactose

ethyl 2,3,4-tri-O-acetyl-1-thio-β-L-fucopyranoside

1,2,3,4-tetra-O-acetyl-L-fucopyranose

Downstream raw materials:

(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

(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

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