(E)-3-{(2R,3S)-3-[(4R,5R)-5-(Benzyloxycarbonylamino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxiranyl}-acrylic acid ethyl ester

Base Information

Chemical Name:(E)-3-{(2R,3S)-3-[(4R,5R)-5-(Benzyloxycarbonylamino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxiranyl}-acrylic acid ethyl ester
CAS No.:98393-47-6
Molecular Formula:C₂₁H₂₇NO₇
Molecular Weight:405.448
Hs Code.:

Synonyms:(E)-3-{(2R,3S)-3-[(4R,5R)-5-(Benzyloxycarbonylamino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxiranyl}-acrylic acid ethyl ester

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Chemical Property of (E)-3-{(2R,3S)-3-[(4R,5R)-5-(Benzyloxycarbonylamino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxiranyl}-acrylic acid ethyl ester

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Technology Process of (E)-3-{(2R,3S)-3-[(4R,5R)-5-(Benzyloxycarbonylamino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxiranyl}-acrylic acid ethyl ester

There total 7 articles about (E)-3-{(2R,3S)-3-[(4R,5R)-5-(Benzyloxycarbonylamino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxiranyl}-acrylic acid ethyl 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:

: 35023-80-4
2,3:5,6-di-O-isopropylidene-D-mannose oxime

: 98393-47-6
(E)-3-{(2R,3S)-3-[(4R,5R)-5-(Benzyloxycarbonylamino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxiranyl}-acrylic acid ethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 100 percent / LiAlH₄ / tetrahydrofuran / Ambient temperature

2: 100 percent / tetrahydrofuran; H₂O / 0 °C

3: 95 percent / pyridine / 0 °C

4: TsOH / methanol; H₂O / 72 h / Ambient temperature

5: amberlite IRA-400/OH^(1-)

6: Collins reagent / CH₂Cl₂ / 5 °C

7: tetrahydrofuran / 0 °C

With pyridine; lithium aluminium tetrahydride; Collins oxidation agent; Amberlite IRA-400; hydroxide; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1021/jo00220a063

Reference yield:

: 98362-05-1
(R)-((4S,5R)-5-Aminomethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol

: 98393-47-6
(E)-3-{(2R,3S)-3-[(4R,5R)-5-(Benzyloxycarbonylamino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxiranyl}-acrylic acid ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 100 percent / tetrahydrofuran; H₂O / 0 °C

2: 95 percent / pyridine / 0 °C

3: TsOH / methanol; H₂O / 72 h / Ambient temperature

4: amberlite IRA-400/OH^(1-)

5: Collins reagent / CH₂Cl₂ / 5 °C

6: tetrahydrofuran / 0 °C

With pyridine; Collins oxidation agent; Amberlite IRA-400; hydroxide; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1021/jo00220a063

Reference yield:

: 98362-01-7,102518-70-7,108341-31-7
[(4R,5R)-5-((2S,3R)-3-Hydroxymethyl-oxiranyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl]-carbamic acid benzyl ester

: 98393-47-6
(E)-3-{(2R,3S)-3-[(4R,5R)-5-(Benzyloxycarbonylamino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxiranyl}-acrylic acid ethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: Collins reagent / CH₂Cl₂ / 5 °C

2: tetrahydrofuran / 0 °C

With Collins oxidation agent; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo00220a063