Acetic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-((1S,2R,3R)-2-benzyloxy-3-hydroxy-1,3-dimethyl-pent-4-enyl)-6-methoxy-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:Acetic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-((1S,2R,3R)-2-benzyloxy-3-hydroxy-1,3-dimethyl-pent-4-enyl)-6-methoxy-tetrahydro-pyran-3-yl ester
CAS No.:110045-85-7
Molecular Formula:C₃₆H₄₄O₈
Molecular Weight:604.741
Hs Code.:

Acetic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-((1S,2R,3R)-2-benzyloxy-3-hydroxy-1,3-dimethyl-pent-4-enyl)-6-methoxy-tetrahydro-pyran-3-yl ester

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Chemical Property of Acetic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-((1S,2R,3R)-2-benzyloxy-3-hydroxy-1,3-dimethyl-pent-4-enyl)-6-methoxy-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-((1S,2R,3R)-2-benzyloxy-3-hydroxy-1,3-dimethyl-pent-4-enyl)-6-methoxy-tetrahydro-pyran-3-yl ester

There total 6 articles about Acetic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-((1S,2R,3R)-2-benzyloxy-3-hydroxy-1,3-dimethyl-pent-4-enyl)-6-methoxy-tetrahydro-pyran-3-yl 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:

: 110045-79-9
methyl-(1) 3,4-dimethoxybenzyl-(8)(8R)-2,3-di-O-benzyl-6-deoxy-6-C-methyl-β-L-threo-D-gluco-octodialdo-1,5:8,4-dipyranoside

: 110045-85-7
Acetic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-((1S,2R,3R)-2-benzyloxy-3-hydroxy-1,3-dimethyl-pent-4-enyl)-6-methoxy-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) NaH, 2.) tetra-n-butylammonium iodide / 1.) DMF, 0 deg C, 20 min, 2.) DMF, RT, 45 min

2: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / CH₂Cl₂; dioxane; H₂O / 4 h / Ambient temperature

3: pyridinium chlorochromate (PCC), Celite, Florisil, sodium acetate / CH₂Cl₂ / Ambient temperature

4: 72 percent / diethyl ether / -78 - -60 °C

5: 53 percent / tetrahydrofuran / -78 - 0 °C

6: 4-(dimethylamino)pyridine / ethyl acetate / Ambient temperature

With dmap; florisil; Celite; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water; ethyl acetate;
DOI:10.1021/jo00229a015

Reference yield:

: 110045-81-3
methyl 2,3,7-tri-O-benzyl-6-deoxy-6-C-methyl-L-threo-α-D-gluco-octapyranosiduronic acid γ-lactone

: 110045-85-7
Acetic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-((1S,2R,3R)-2-benzyloxy-3-hydroxy-1,3-dimethyl-pent-4-enyl)-6-methoxy-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 72 percent / diethyl ether / -78 - -60 °C

2: 53 percent / tetrahydrofuran / -78 - 0 °C

3: 4-(dimethylamino)pyridine / ethyl acetate / Ambient temperature

With dmap; In tetrahydrofuran; diethyl ether; ethyl acetate;
DOI:10.1021/jo00229a015

Reference yield:

: (2R,3R,4S,4aR,6S,7R,8S,8aR)-3,7,8-Tris-benzyloxy-6-methoxy-4-methyl-octahydro-pyrano[3,2-b]pyran-2-ol

: 110045-85-7
Acetic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-((1S,2R,3R)-2-benzyloxy-3-hydroxy-1,3-dimethyl-pent-4-enyl)-6-methoxy-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: pyridinium chlorochromate (PCC), Celite, Florisil, sodium acetate / CH₂Cl₂ / Ambient temperature

2: 72 percent / diethyl ether / -78 - -60 °C

3: 53 percent / tetrahydrofuran / -78 - 0 °C

4: 4-(dimethylamino)pyridine / ethyl acetate / Ambient temperature

With dmap; florisil; Celite; sodium acetate; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate;
DOI:10.1021/jo00229a015