(2S,3S,4R,5R,6R)-6-((2R,3R,4R,5R,6R)-3-Acetylamino-2,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy)-3,4-bis-benzyloxy-5-hydroxy-tetrahydro-pyran-2-carboxylic acid

Base Information

Chemical Name:(2S,3S,4R,5R,6R)-6-((2R,3R,4R,5R,6R)-3-Acetylamino-2,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy)-3,4-bis-benzyloxy-5-hydroxy-tetrahydro-pyran-2-carboxylic acid
CAS No.:303128-09-8
Molecular Formula:C₄₂H₄₇NO₁₂
Molecular Weight:757.835
Hs Code.:

(2S,3S,4R,5R,6R)-6-((2R,3R,4R,5R,6R)-3-Acetylamino-2,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy)-3,4-bis-benzyloxy-5-hydroxy-tetrahydro-pyran-2-carboxylic acid

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Chemical Property of (2S,3S,4R,5R,6R)-6-((2R,3R,4R,5R,6R)-3-Acetylamino-2,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy)-3,4-bis-benzyloxy-5-hydroxy-tetrahydro-pyran-2-carboxylic acid

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Technology Process of (2S,3S,4R,5R,6R)-6-((2R,3R,4R,5R,6R)-3-Acetylamino-2,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy)-3,4-bis-benzyloxy-5-hydroxy-tetrahydro-pyran-2-carboxylic acid

There total 23 articles about (2S,3S,4R,5R,6R)-6-((2R,3R,4R,5R,6R)-3-Acetylamino-2,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy)-3,4-bis-benzyloxy-5-hydroxy-tetrahydro-pyran-2-carboxylic acid 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:

: (2S,3S,4S,5R,6R)-6-((2R,3R,4R,5R,6R)-3-Acetylamino-2,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy)-5-benzoyloxy-3,4-bis-benzyloxy-tetrahydro-pyran-2-carboxylic acid

: 303128-09-8
(2S,3S,4R,5R,6R)-6-((2R,3R,4R,5R,6R)-3-Acetylamino-2,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy)-3,4-bis-benzyloxy-5-hydroxy-tetrahydro-pyran-2-carboxylic acid

Guidance literature:: With sodium hydroxide; In tetrahydrofuran; methanol; at 20 ℃; for 6h;
DOI:10.1039/b002835p

Reference yield:

: 100-39-0
benzyl bromide

: 303128-09-8
(2S,3S,4R,5R,6R)-6-((2R,3R,4R,5R,6R)-3-Acetylamino-2,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy)-3,4-bis-benzyloxy-5-hydroxy-tetrahydro-pyran-2-carboxylic acid

Guidance literature:: Multi-step reaction with 8 steps

1.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

1.2: 81 percent / TBAI / tetrahydrofuran / 5 h / 0 - 20 °C

2.1: methanol / 48 h

3.1: 2.45 g / imidazole / dimethylformamide / 0.67 h / 0 °C

4.1: 62 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂; toluene / 0.5 h / 20 °C

5.1: 92 percent / tributylstannane; azoisobutyronitrile / benzene / 1.5 h / 20 °C

6.1: 82 percent / aq. AcOH / tetrahydrofuran / 72 h / 20 °C

7.1: aq. H₂O₂; LiOH / tetrahydrofuran / 16 h / 0 - 20 °C

8.1: 484 mg / aq. NaOH / tetrahydrofuran; methanol / 6 h / 20 °C

With 1H-imidazole; lithium hydroxide; sodium hydroxide; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; dihydrogen peroxide; tri-n-butyl-tin hydride; sodium hydride; acetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 1.1: Metallation / 1.2: Etherification / 2.1: Substitution / 3.1: Substitution / 4.1: Substitution / 5.1: Reduction / 6.1: Hydrolysis / 7.1: Hydrolysis / 8.1: Hydrolysis;
DOI:10.1039/b002835p

Reference yield:

: 39686-94-7,56632-47-4,65827-58-9,99202-62-7,99202-66-1,103082-79-7,103703-00-0,103703-01-1,118711-49-2,127853-23-0,139563-66-9
1,2,4,6-tetra-O-acetyl-3-O-benzyl-β-D-glucopyranose

: 303128-09-8
(2S,3S,4R,5R,6R)-6-((2R,3R,4R,5R,6R)-3-Acetylamino-2,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy)-3,4-bis-benzyloxy-5-hydroxy-tetrahydro-pyran-2-carboxylic acid

Guidance literature:: Multi-step reaction with 13 steps

1.1: 69 percent / trimethylsilyl triflate; 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / 0 °C

2.1: 89 percent / methanol / 16 h / 20 °C

3.1: 84 percent / CF₃CO₂H / 0.33 h

4.1: 83 percent / pyridine / CH₂Cl₂ / 1.5 h / 0 - 20 °C

5.1: 64 percent / AlCl₃; borane-trimethylamine complex; 4 Angstroem molecular sieves / diethyl ether; CH₂Cl₂ / 2 h / 0 °C

6.1: 79 percent / CrO₃; H₂SO₄ / acetone / 1 h / 20 °C

7.1: 1.56 g / DMAP; Et₃N / CH₂Cl₂ / 2 h / 0 - 20 °C

8.1: cerium(IV) ammonium nitrite / H₂O; acetonitrile; toluene / 0.33 h / 20 °C

8.2: 71 percent / DBU / CH₂Cl₂ / 0.17 h / 0 °C

9.1: 62 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂; toluene / 0.5 h / 20 °C

10.1: 92 percent / tributylstannane; azoisobutyronitrile / benzene / 1.5 h / 20 °C

11.1: 82 percent / aq. AcOH / tetrahydrofuran / 72 h / 20 °C

12.1: aq. H₂O₂; LiOH / tetrahydrofuran / 16 h / 0 - 20 °C

13.1: 484 mg / aq. NaOH / tetrahydrofuran; methanol / 6 h / 20 °C

With pyridine; chromium(VI) oxide; dmap; lithium hydroxide; sodium hydroxide; aluminium trichloride; ammonium cerium(IV) nitrate; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; trimethylamine-borane; 4 A molecular sieve; sulfuric acid; dihydrogen peroxide; tri-n-butyl-tin hydride; acetic acid; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetone; toluene; acetonitrile; benzene; 1.1: Etherification / 2.1: Deacetylation / 3.1: Cyclization / 4.1: Acylation / 5.1: Ring cleavage / 6.1: Oxidation / 7.1: Acylation / 8.1: Substitution / 8.2: Addition / 9.1: Substitution / 10.1: Reduction / 11.1: Hydrolysis / 12.1: Hydrolysis / 13.1: Hydrolysis;
DOI:10.1039/b002835p