(2R,3S,4S,5R,6S)-4-Benzyloxy-3-(2-chloro-acetoxy)-5-(2,2-dimethyl-propionyloxy)-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

Chemical Name:(2R,3S,4S,5R,6S)-4-Benzyloxy-3-(2-chloro-acetoxy)-5-(2,2-dimethyl-propionyloxy)-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester
CAS No.:198200-59-8
Molecular Formula:C₂₂H₂₉ClO₉
Molecular Weight:472.92
Hs Code.:

Synonyms:(2R,3S,4S,5R,6S)-4-Benzyloxy-3-(2-chloro-acetoxy)-5-(2,2-dimethyl-propionyloxy)-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

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Chemical Property of (2R,3S,4S,5R,6S)-4-Benzyloxy-3-(2-chloro-acetoxy)-5-(2,2-dimethyl-propionyloxy)-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

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Technology Process of (2R,3S,4S,5R,6S)-4-Benzyloxy-3-(2-chloro-acetoxy)-5-(2,2-dimethyl-propionyloxy)-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 16 articles about (2R,3S,4S,5R,6S)-4-Benzyloxy-3-(2-chloro-acetoxy)-5-(2,2-dimethyl-propionyloxy)-6-methoxy-tetrahydro-pyran-2-carboxylic 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: 92.0%

: 541-88-8
Chloroacetic anhydride

: (2R,3S,4S,5R,6S)-4-Benzyloxy-5-(2,2-dimethyl-propionyloxy)-3-hydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

: 198200-59-8
(2R,3S,4S,5R,6S)-4-Benzyloxy-3-(2-chloro-acetoxy)-5-(2,2-dimethyl-propionyloxy)-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: With pyridine; at 0 ℃; for 0.5h;
DOI:10.1016/S0008-6215(97)00149-3

Reference yield:

: 198200-41-8
(2S,3R,4S,5S)-4-Benzyloxy-2-methoxy-6-methylene-tetrahydro-pyran-3,5-diol

: 198200-59-8
(2R,3S,4S,5R,6S)-4-Benzyloxy-3-(2-chloro-acetoxy)-5-(2,2-dimethyl-propionyloxy)-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 77 percent / 4 Angstroem molecular sieves, pyridine / 3 h / 0 °C

2: 89 percent / imidazole / dimethylformamide / 2.5 h / Ambient temperature

3: 41 percent / diborane*THF / tetrahydrofuran / 4 h / Ambient temperature

4: chromium trioxide, conc. H₂SO₄ / H₂O; acetone / 0 °C

5: Et₃N, DMAP / CH₂Cl₂ / 2 h / 0 °C

6: Bu₄NF / tetrahydrofuran / 0.67 h / 0 °C

7: 92 percent / pyridine / 0.5 h / 0 °C

With pyridine; 1H-imidazole; chromium(VI) oxide; dmap; B₂H₆-THF; 4 A molecular sieve; sulfuric acid; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0008-6215(97)00149-3

Reference yield:

: 198200-37-2
methyl 3-O-benzyl-6-deoxy-6-iodo-α-D-glucopyranoside

: 198200-59-8
(2R,3S,4S,5R,6S)-4-Benzyloxy-3-(2-chloro-acetoxy)-5-(2,2-dimethyl-propionyloxy)-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 95 percent / pyridine / 2 h / Ambient temperature

2: 74 percent / DBU / dimethylformamide / 2.5 h / 75 °C

3: 84 percent / NaOMe / methanol / 1.5 h / Ambient temperature

4: 77 percent / 4 Angstroem molecular sieves, pyridine / 3 h / 0 °C

5: 89 percent / imidazole / dimethylformamide / 2.5 h / Ambient temperature

6: 41 percent / diborane*THF / tetrahydrofuran / 4 h / Ambient temperature

7: chromium trioxide, conc. H₂SO₄ / H₂O; acetone / 0 °C

8: Et₃N, DMAP / CH₂Cl₂ / 2 h / 0 °C

9: Bu₄NF / tetrahydrofuran / 0.67 h / 0 °C

10: 92 percent / pyridine / 0.5 h / 0 °C

With pyridine; 1H-imidazole; chromium(VI) oxide; dmap; B₂H₆-THF; 4 A molecular sieve; sulfuric acid; tetrabutyl ammonium fluoride; sodium methylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0008-6215(97)00149-3