(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

Base Information

• Chemical Name: (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
• CAS No.: 289634-87-3
• Molecular Formula: C₃₈H₄₃NO₉
• Molecular Weight: 657.761

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (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

There total 6 articles about (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 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)-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)

Guidance literature:

Multi-step reaction with 6 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

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

Guidance literature:

Multi-step reaction with 4 steps

1: NaOMe, MeOH / 20 °C

2: p-TsOH*H₂O / CH₂Cl₂ / 20 °C

3: 84 percent / NaH, TBAI / tetrahydrofuran

4: CuBr₂, TBAI / CH₂Cl₂; dimethylformamide

With methanol; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; copper(ll) bromide; In tetrahydrofuran; dichloromethane; 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)-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)

Guidance literature:

Multi-step reaction with 5 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

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

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

upstream raw materials:

N-(9-fluorenylmethoxycarbonyl)-L-threonine allyl ester

ethyl 2-O-benzyl-3,4-O-isopropylidene-1-thio-β-L-fucopyranoside

6-deoxy-L-galactose

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

Downstream raw materials:

(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

(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)-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

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