(2R,3S,4R,5R,6R)-3-((2R,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-[5-(2-benzyloxycarbonylamino-ethanesulfonyl)-pentyloxy]-5-hydroxy-tetrahydro-pyran-2-carboxylic acid

Base Information

Chemical Name:(2R,3S,4R,5R,6R)-3-((2R,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-[5-(2-benzyloxycarbonylamino-ethanesulfonyl)-pentyloxy]-5-hydroxy-tetrahydro-pyran-2-carboxylic acid
CAS No.:920957-79-5
Molecular Formula:C₄₈H₅₈N₄O₁₅S
Molecular Weight:963.072
Hs Code.:

(2R,3S,4R,5R,6R)-3-((2R,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-[5-(2-benzyloxycarbonylamino-ethanesulfonyl)-pentyloxy]-5-hydroxy-tetrahydro-pyran-2-carboxylic acid

Synonyms:(2R,3S,4R,5R,6R)-3-((2R,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-[5-(2-benzyloxycarbonylamino-ethanesulfonyl)-pentyloxy]-5-hydroxy-tetrahydro-pyran-2-carboxylic acid

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Chemical Property of (2R,3S,4R,5R,6R)-3-((2R,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-[5-(2-benzyloxycarbonylamino-ethanesulfonyl)-pentyloxy]-5-hydroxy-tetrahydro-pyran-2-carboxylic acid

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Technology Process of (2R,3S,4R,5R,6R)-3-((2R,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-[5-(2-benzyloxycarbonylamino-ethanesulfonyl)-pentyloxy]-5-hydroxy-tetrahydro-pyran-2-carboxylic acid

There total 6 articles about (2R,3S,4R,5R,6R)-3-((2R,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-[5-(2-benzyloxycarbonylamino-ethanesulfonyl)-pentyloxy]-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: 73.0%

: 920957-78-4
(2R,3S,4S,5R,6R)-3-((2R,3R,4R,5S,6R)-6-Acetoxymethyl-3-azido-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-[5-(2-benzyloxycarbonylamino-ethylsulfanyl)-pentyloxy]-5-(2,2-dimethyl-propionyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

: 920957-79-5
(2R,3S,4R,5R,6R)-3-((2R,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-[5-(2-benzyloxycarbonylamino-ethanesulfonyl)-pentyloxy]-5-hydroxy-tetrahydro-pyran-2-carboxylic acid

Guidance literature:: (2R,3S,4S,5R,6R)-3-((2R,3R,4R,5S,6R)-6-Acetoxymethyl-3-azido-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-[5-(2-benzyloxycarbonylamino-ethylsulfanyl)-pentyloxy]-5-(2,2-dimethyl-propionyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester; With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; at 20 ℃; for 16h;

With potassium hydroxide; In tetrahydrofuran; methanol; at 20 ℃; for 16h; Further stages.;
DOI:10.1002/chem.200601103

Reference yield:

: 920957-77-3
(2R,3S,4S,5R,6R)-4-Benzyloxy-5-(2,2-dimethyl-propionyloxy)-3-hydroxy-6-pent-4-enyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

: 920957-79-5
(2R,3S,4R,5R,6R)-3-((2R,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-[5-(2-benzyloxycarbonylamino-ethanesulfonyl)-pentyloxy]-5-hydroxy-tetrahydro-pyran-2-carboxylic acid

Guidance literature:: Multi-step reaction with 3 steps

1.1: 81 percent / TMSOTf / CH₂Cl₂ / 0.5 h / -25 °C

2.1: 78 percent / AIBN / tetrahydrofuran / 12 h / 75 °C

3.1: aq. H₂O₂; aq. LiOH / tetrahydrofuran / 16 h / 20 °C

3.2: 73 percent / aq. KOH / tetrahydrofuran; methanol / 16 h / 20 °C

With lithium hydroxide; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; dihydrogen peroxide; In tetrahydrofuran; dichloromethane;
DOI:10.1002/chem.200601103

Reference yield:

: 920957-76-2
(2R,3S,4S,5R,6R)-4-Benzyloxy-5-(2,2-dimethyl-propionyloxy)-3-(4-oxo-pentanoyloxy)-6-pent-4-enyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

: 920957-79-5
(2R,3S,4R,5R,6R)-3-((2R,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-[5-(2-benzyloxycarbonylamino-ethanesulfonyl)-pentyloxy]-5-hydroxy-tetrahydro-pyran-2-carboxylic acid

Guidance literature:: Multi-step reaction with 4 steps

1.1: 91 percent / pyridine; acetic acid; hydrazine monohydrate / CH₂Cl₂ / 1.5 h / 20 °C

2.1: 81 percent / TMSOTf / CH₂Cl₂ / 0.5 h / -25 °C

3.1: 78 percent / AIBN / tetrahydrofuran / 12 h / 75 °C

4.1: aq. H₂O₂; aq. LiOH / tetrahydrofuran / 16 h / 20 °C

4.2: 73 percent / aq. KOH / tetrahydrofuran; methanol / 16 h / 20 °C

With pyridine; lithium hydroxide; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; dihydrogen peroxide; hydrazine hydrate; acetic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1002/chem.200601103