Benzoic acid (2R,3R,4S,5R,6R)-4-azido-2-hydroxymethyl-6-methoxy-5-methoxycarbonylmethoxy-tetrahydro-pyran-3-yl ester

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Chemical Name:Benzoic acid (2R,3R,4S,5R,6R)-4-azido-2-hydroxymethyl-6-methoxy-5-methoxycarbonylmethoxy-tetrahydro-pyran-3-yl ester
CAS No.:251323-99-6
Molecular Formula:C₁₇H₂₁N₃O₈
Molecular Weight:395.369
Hs Code.:

Synonyms:Benzoic acid (2R,3R,4S,5R,6R)-4-azido-2-hydroxymethyl-6-methoxy-5-methoxycarbonylmethoxy-tetrahydro-pyran-3-yl ester

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Chemical Property of Benzoic acid (2R,3R,4S,5R,6R)-4-azido-2-hydroxymethyl-6-methoxy-5-methoxycarbonylmethoxy-tetrahydro-pyran-3-yl ester

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Technology Process of Benzoic acid (2R,3R,4S,5R,6R)-4-azido-2-hydroxymethyl-6-methoxy-5-methoxycarbonylmethoxy-tetrahydro-pyran-3-yl ester

There total 10 articles about Benzoic acid (2R,3R,4S,5R,6R)-4-azido-2-hydroxymethyl-6-methoxy-5-methoxycarbonylmethoxy-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: 95.0%

: 251323-98-5
Benzoic acid (2R,3R,4S,5R,6R)-4-azido-6-methoxy-2-(4-methoxy-benzyloxymethyl)-5-methoxycarbonylmethoxy-tetrahydro-pyran-3-yl ester

: 251323-99-6
Benzoic acid (2R,3R,4S,5R,6R)-4-azido-2-hydroxymethyl-6-methoxy-5-methoxycarbonylmethoxy-tetrahydro-pyran-3-yl ester

Guidance literature:: With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; for 2h;
DOI:10.1016/S0960-894X(03)00384-6

Reference yield:

: 65784-76-1
methyl 3-azido-3-deoxy-β-D-glucopyranoside

: 251323-99-6
Benzoic acid (2R,3R,4S,5R,6R)-4-azido-2-hydroxymethyl-6-methoxy-5-methoxycarbonylmethoxy-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 68 percent / p-toluenesulfonic acid monohydrate / dimethylformamide / 4 h

2: 80 percent / Ag₂O; KI / dimethylformamide / 16 h

3: 22 percent / NaBH₃CN; Me₃SiCl; 3 Angstroem molecular sieves / acetonitrile / 4 h

4: pyridine / CH₂Cl₂ / 2 h / 0 °C

5: toluene / 1 h

6: 95 percent / DDQ; H₂O / CH₂Cl₂ / 2 h

With pyridine; chloro-trimethyl-silane; 3 A molecular sieve; water; sodium cyanoborohydride; toluene-4-sulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; potassium iodide; silver(l) oxide; In dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1016/S0960-894X(03)00384-6

Reference yield:

: 185114-94-7,155417-78-0
1,2,4,6-Tetra-O-acetyl-3-azido-3-deoxy-α/β-gluco-hexopyranose

: 251323-99-6
Benzoic acid (2R,3R,4S,5R,6R)-4-azido-2-hydroxymethyl-6-methoxy-5-methoxycarbonylmethoxy-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 9 steps

1: Me₃SiBr; BiBr₃ / CH₂Cl₂ / 4 h

2: Ag₂O; CaSO₄ / CH₂Cl₂ / 1 h

3: MeONa; MeOH / 4 h

4: 68 percent / p-toluenesulfonic acid monohydrate / dimethylformamide / 4 h

5: 80 percent / Ag₂O; KI / dimethylformamide / 16 h

6: 22 percent / NaBH₃CN; Me₃SiCl; 3 Angstroem molecular sieves / acetonitrile / 4 h

7: pyridine / CH₂Cl₂ / 2 h / 0 °C

8: toluene / 1 h

9: 95 percent / DDQ; H₂O / CH₂Cl₂ / 2 h

With pyridine; methanol; calcium sulfate; chloro-trimethyl-silane; bismuth(III) bromide; trimethylsilyl bromide; 3 A molecular sieve; water; sodium methylate; sodium cyanoborohydride; toluene-4-sulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; potassium iodide; silver(l) oxide; In dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1016/S0960-894X(03)00384-6