(2S,4R,5R,6R)-5-((2R,3R,4R,5S,6R)-6-Acetoxymethyl-3-acetylamino-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-2-(3-benzyloxycarbonylamino-propoxy)-6-((R)-1,2-dihydroxy-ethyl)-tetrahydro-pyran-2-carboxylic acid ethyl ester

Base Information

Chemical Name:(2S,4R,5R,6R)-5-((2R,3R,4R,5S,6R)-6-Acetoxymethyl-3-acetylamino-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-2-(3-benzyloxycarbonylamino-propoxy)-6-((R)-1,2-dihydroxy-ethyl)-tetrahydro-pyran-2-carboxylic acid ethyl ester
CAS No.:142889-24-5
Molecular Formula:C₅₂H₆₄N₂O₁₆
Molecular Weight:973.084
Hs Code.:

(2S,4R,5R,6R)-5-((2R,3R,4R,5S,6R)-6-Acetoxymethyl-3-acetylamino-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-2-(3-benzyloxycarbonylamino-propoxy)-6-((R)-1,2-dihydroxy-ethyl)-tetrahydro-pyran-2-carboxylic acid ethyl ester

Synonyms:(2S,4R,5R,6R)-5-((2R,3R,4R,5S,6R)-6-Acetoxymethyl-3-acetylamino-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-2-(3-benzyloxycarbonylamino-propoxy)-6-((R)-1,2-dihydroxy-ethyl)-tetrahydro-pyran-2-carboxylic acid ethyl ester

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Chemical Property of (2S,4R,5R,6R)-5-((2R,3R,4R,5S,6R)-6-Acetoxymethyl-3-acetylamino-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-2-(3-benzyloxycarbonylamino-propoxy)-6-((R)-1,2-dihydroxy-ethyl)-tetrahydro-pyran-2-carboxylic acid ethyl ester

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Technology Process of (2S,4R,5R,6R)-5-((2R,3R,4R,5S,6R)-6-Acetoxymethyl-3-acetylamino-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-2-(3-benzyloxycarbonylamino-propoxy)-6-((R)-1,2-dihydroxy-ethyl)-tetrahydro-pyran-2-carboxylic acid ethyl ester

There total 14 articles about (2S,4R,5R,6R)-5-((2R,3R,4R,5S,6R)-6-Acetoxymethyl-3-acetylamino-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-2-(3-benzyloxycarbonylamino-propoxy)-6-((R)-1,2-dihydroxy-ethyl)-tetrahydro-pyran-2-carboxylic acid ethyl 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:

: 55682-48-9
1,6-anhydro-2-azido-3,4-di-O-benzyl-2-deoxy-D-glucopyranose

: 142889-24-5
(2S,4R,5R,6R)-5-((2R,3R,4R,5S,6R)-6-Acetoxymethyl-3-acetylamino-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-2-(3-benzyloxycarbonylamino-propoxy)-6-((R)-1,2-dihydroxy-ethyl)-tetrahydro-pyran-2-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 95 percent / CF₃COOH / 4 h / 50 °C

2: 71 percent / BF₃*OEt₂ / 1,2-dichloro-ethane / 1 h / 35 °C

3: 70 percent / N-iodosuccinimide, molecular sieves, triflic acid / 1,2-dichloro-ethane; diethyl ether / 0.25 h

4: H₂S, Et₃N / H₂O; pyridine / 1 h

5: pyridine / 4 h

6: AcOH / H₂O / 4 h

With pyridine; N-iodo-succinimide; molecular sieve; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; hydrogen sulfide; acetic acid; triethylamine; trifluoroacetic acid; In pyridine; diethyl ether; water; 1,2-dichloro-ethane;
DOI:10.1016/S0040-4020(01)81239-4

Reference yield:

: 142889-23-4
ethyl (N-benzyloxycarbonyl-3-aminopropyl 5-O-(2-acetamido-6-O-acetyl-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-4-O-benzyl-3-deoxy-7,8-O-isopropylidene-β-D-manno-2-octulopyranosid)onate

: 142889-24-5
(2S,4R,5R,6R)-5-((2R,3R,4R,5S,6R)-6-Acetoxymethyl-3-acetylamino-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-2-(3-benzyloxycarbonylamino-propoxy)-6-((R)-1,2-dihydroxy-ethyl)-tetrahydro-pyran-2-carboxylic acid ethyl ester

Guidance literature:: With acetic acid; In water; for 4h;
DOI:10.1016/S0040-4020(01)81239-4

Reference yield:

: 100-39-0
benzyl bromide

: 142889-24-5
(2S,4R,5R,6R)-5-((2R,3R,4R,5S,6R)-6-Acetoxymethyl-3-acetylamino-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-2-(3-benzyloxycarbonylamino-propoxy)-6-((R)-1,2-dihydroxy-ethyl)-tetrahydro-pyran-2-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 100 percent / NaH / dimethylformamide / 1 h

2: 95 percent / CF₃COOH / 4 h / 50 °C

3: 71 percent / BF₃*OEt₂ / 1,2-dichloro-ethane / 1 h / 35 °C

4: 70 percent / N-iodosuccinimide, molecular sieves, triflic acid / 1,2-dichloro-ethane; diethyl ether / 0.25 h

5: H₂S, Et₃N / H₂O; pyridine / 1 h

6: pyridine / 4 h

7: AcOH / H₂O / 4 h

With pyridine; N-iodo-succinimide; molecular sieve; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; hydrogen sulfide; sodium hydride; acetic acid; triethylamine; trifluoroacetic acid; In pyridine; diethyl ether; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)81239-4