Malonic acid (3aR,4R,6R,6aR)-6-(3-benzyloxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester (2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester

Base Information

Chemical Name:Malonic acid (3aR,4R,6R,6aR)-6-(3-benzyloxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester (2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester
CAS No.:191479-28-4
Molecular Formula:C₅₇H₆₀N₂O₁₅
Molecular Weight:1013.11
Hs Code.:

Malonic acid (3aR,4R,6R,6aR)-6-(3-benzyloxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester (2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester

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Chemical Property of Malonic acid (3aR,4R,6R,6aR)-6-(3-benzyloxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester (2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester

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Technology Process of Malonic acid (3aR,4R,6R,6aR)-6-(3-benzyloxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester (2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester

There total 5 articles about Malonic acid (3aR,4R,6R,6aR)-6-(3-benzyloxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester (2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-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: 52.0%

: 74808-09-6,83441-60-5,90357-89-4,90358-01-3,103368-01-0,103368-04-3,103368-06-5,104048-30-8,104048-33-1,132201-75-3,132748-02-8,114743-70-3
2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl trichloroacetimidate

: 191479-27-3
Malonic acid mono-[(3aR,4R,6R,6aR)-6-(3-benzyloxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl] ester

: 191479-28-4
Malonic acid (3aR,4R,6R,6aR)-6-(3-benzyloxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester (2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester

Guidance literature:: In dichloromethane; at -20 - 20 ℃;
DOI:10.1016/S0968-0896(97)00005-9

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 191479-28-4
Malonic acid (3aR,4R,6R,6aR)-6-(3-benzyloxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester (2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 89 percent / i-Pr₂NEt / CH₂Cl₂ / 4 h / Ambient temperature

2: 94 percent / Bu₄NF / tetrahydrofuran / 3 h

3: 77 percent / 1.5 h / 100 °C

4: 52 percent / CH₂Cl₂ / -20 - 20 °C

With tetrabutyl ammonium fluoride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0968-0896(97)00005-9

Reference yield:

: 102147-76-2
5'-O-(t-butyldimethylsilyl)-2',3'-O-isopropylideneuridine

: 191479-28-4
Malonic acid (3aR,4R,6R,6aR)-6-(3-benzyloxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester (2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 89 percent / i-Pr₂NEt / CH₂Cl₂ / 4 h / Ambient temperature

2: 94 percent / Bu₄NF / tetrahydrofuran / 3 h

3: 77 percent / 1.5 h / 100 °C

4: 52 percent / CH₂Cl₂ / -20 - 20 °C

With tetrabutyl ammonium fluoride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0968-0896(97)00005-9