3-((3aS,5R,6R,6aS)-6-benzyloxy-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(diethoxyphosphoryl)propionic acid methyl ester

Base Information

Chemical Name:3-((3aS,5R,6R,6aS)-6-benzyloxy-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(diethoxyphosphoryl)propionic acid methyl ester
CAS No.:866878-98-0
Molecular Formula:C₂₂H₃₃O₉P
Molecular Weight:472.472
Hs Code.:

Synonyms:3-((3aS,5R,6R,6aS)-6-benzyloxy-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(diethoxyphosphoryl)propionic acid methyl ester

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Chemical Property of 3-((3aS,5R,6R,6aS)-6-benzyloxy-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(diethoxyphosphoryl)propionic acid methyl ester

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Technology Process of 3-((3aS,5R,6R,6aS)-6-benzyloxy-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(diethoxyphosphoryl)propionic acid methyl ester

There total 2 articles about 3-((3aS,5R,6R,6aS)-6-benzyloxy-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(diethoxyphosphoryl)propionic acid methyl 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: 73.0%

: 1067-74-9
Methyl diethylphosphonoacetate

: 895558-57-3
((3aS,5R,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl trifluoromethanesulphonate

: 866878-98-0
3-((3aS,5R,6R,6aS)-6-benzyloxy-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(diethoxyphosphoryl)propionic acid methyl ester

Guidance literature:: Methyl diethylphosphonoacetate; With sodium hydride; In N,N-dimethyl-formamide;

((3aS,5R,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl trifluoromethanesulphonate; With 15-crown-5; In N,N-dimethyl-formamide; at 20 ℃;
DOI:10.1021/ja052929v

Reference yield:

: 19139-80-1,34370-91-7,68354-70-1,70798-12-8,59358-33-7
((3aS,5R,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol

: 866878-98-0
3-((3aS,5R,6R,6aS)-6-benzyloxy-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(diethoxyphosphoryl)propionic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 93 percent / pyridine / CH₂Cl₂ / 0.25 h / -30 °C

2.1: NaH / dimethylformamide

2.2: 73 percent / 15-crown-5 / dimethylformamide / 20 °C

With pyridine; sodium hydride; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja052929v

Reference yield:

: 866878-98-0
3-((3aS,5R,6R,6aS)-6-benzyloxy-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(diethoxyphosphoryl)propionic acid methyl ester

: 866879-12-1
methyl [4-2H]shikimate

Guidance literature:: Multi-step reaction with 6 steps

1: aq. ammonium formate / Pd/C / methanol / 2 h / 50 °C

2: P₂O₅; DMSO / dimethylformamide / 3.5 h / 70 °C

3: aq. NaBD₄ / methanol / 1 h / 0 °C

4: Dowex-50Wx₈-200 / acetone / 20 °C

5: 132 mg / NaOMe / methanol / 20 °C

6: 74 percent / Dowex-50WX₈-200 / methanol; H₂O / 20 °C

With sodium borodeuteride; Dowex-50WX₈-200; sodium methylate; ammonium formate; phosphorus pentoxide; dimethyl sulfoxide; palladium on activated charcoal; In methanol; water; N,N-dimethyl-formamide; acetone;
DOI:10.1021/ja052929v