{2-[((S)-2-Azido-3-{(2-cyano-ethoxy)-[(2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-tetrahydro-pyran-2-ylmethoxy]-phosphoryloxy}-propoxy)-(2-cyano-ethoxy)-phosphoryloxy]-ethyl}-trimethyl-ammonium

Base Information

• Chemical Name: {2-[((S)-2-Azido-3-{(2-cyano-ethoxy)-[(2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-tetrahydro-pyran-2-ylmethoxy]-phosphoryloxy}-propoxy)-(2-cyano-ethoxy)-phosphoryloxy]-ethyl}-trimethyl-ammonium
• CAS No.: 221697-44-5
• Molecular Formula: C₄₇H₆₅N₆O₁₅P₂
• Molecular Weight: 1016.01

Synonyms:

Chemical Property of {2-[((S)-2-Azido-3-{(2-cyano-ethoxy)-[(2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-tetrahydro-pyran-2-ylmethoxy]-phosphoryloxy}-propoxy)-(2-cyano-ethoxy)-phosphoryloxy]-ethyl}-trimethyl-ammonium

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of {2-[((S)-2-Azido-3-{(2-cyano-ethoxy)-[(2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-tetrahydro-pyran-2-ylmethoxy]-phosphoryloxy}-propoxy)-(2-cyano-ethoxy)-phosphoryloxy]-ethyl}-trimethyl-ammonium

There total 5 articles about {2-[((S)-2-Azido-3-{(2-cyano-ethoxy)-[(2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-tetrahydro-pyran-2-ylmethoxy]-phosphoryloxy}-propoxy)-(2-cyano-ethoxy)-phosphoryloxy]-ethyl}-trimethyl-ammonium 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:

{2-[((S)-2-Azido-3-{(2-cyano-ethoxy)-[(2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-tetrahydro-pyran-2-ylmethoxy]-phosphoryloxy}-propoxy)-(2-cyano-ethoxy)-phosphanyloxy]-ethyl}-trimethyl-ammonium → {2-[((S)-2-Azido-3-{(2-cyano-ethoxy)-[(2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-tetrahydro-pyran-2-ylmethoxy]-phosphoryloxy}-propoxy)-(2-cyano-ethoxy)-phosphoryloxy]-ethyl}-trimethyl-ammonium (221697-44-5)

Guidance literature:

With silver(II) bis(pyridine-2,6-dicarboxylate); In methanol; water; acetonitrile; Yield given; Ambient temperature;

DOI:10.1016/S0040-4039(99)00191-4

Reference yield:

3-O-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-1,2-O-isopropylidene-L-glycerol (65751-66-8) → {2-[((S)-2-Azido-3-{(2-cyano-ethoxy)-[(2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-tetrahydro-pyran-2-ylmethoxy]-phosphoryloxy}-propoxy)-(2-cyano-ethoxy)-phosphoryloxy]-ethyl}-trimethyl-ammonium (221697-44-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 1H-tetrazole, MS₄A / CH₂Cl₂ / 0 °C

2: silver(II) bis(pyridine-2,6-dicarboxylate)monohydrate / acetonitrile; H₂O; methanol / Ambient temperature

3: 1H-tetrazole, MS₄A / CH₂Cl₂ / 0 °C

4: silver(II) bis(pyridine-2,6-dicarboxylate)monohydrate / acetonitrile; H₂O; methanol / Ambient temperature

With 1H-tetrazole; silver(II) bis(pyridine-2,6-dicarboxylate); In methanol; dichloromethane; water; acetonitrile;

DOI:10.1016/S0040-4039(99)00191-4

Reference yield:

[(2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-((R)-1-oxiranylmethoxy)-tetrahydro-pyran-2-yl]-methanol → {2-[((S)-2-Azido-3-{(2-cyano-ethoxy)-[(2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-tetrahydro-pyran-2-ylmethoxy]-phosphoryloxy}-propoxy)-(2-cyano-ethoxy)-phosphoryloxy]-ethyl}-trimethyl-ammonium (221697-44-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) AcOCs, 2.) NaOMe, 3.) p-TsOH / 1.) DMF, 80 deg C, 2.) MeOH, 3.) room temp.

2: 1H-tetrazole, MS₄A / CH₂Cl₂ / 0 °C

3: silver(II) bis(pyridine-2,6-dicarboxylate)monohydrate / acetonitrile; H₂O; methanol / Ambient temperature

4: 1H-tetrazole, MS₄A / CH₂Cl₂ / 0 °C

5: silver(II) bis(pyridine-2,6-dicarboxylate)monohydrate / acetonitrile; H₂O; methanol / Ambient temperature

With 1H-tetrazole; silver(II) bis(pyridine-2,6-dicarboxylate); sodium methylate; cesium acetate; toluene-4-sulfonic acid; In methanol; dichloromethane; water; acetonitrile;

DOI:10.1016/S0040-4039(99)00191-4

upstream raw materials:

3-O-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-1,2-O-isopropylidene-L-glycerol

Phosphoric acid (S)-2-azido-3-hydroxy-propyl ester 2-cyano-ethyl ester (2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-tetrahydro-pyran-2-ylmethyl ester

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