(2S,4S,5R,6R)-5-Acetylamino-4-benzyloxy-2-[(2S,3R,4S,5S,6R)-3-benzyloxy-6-benzyloxymethyl-5-hydroxy-2-(4-methoxy-phenoxy)-tetrahydro-pyran-4-yloxy]-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl ester

Base Information

• Chemical Name: (2S,4S,5R,6R)-5-Acetylamino-4-benzyloxy-2-[(2S,3R,4S,5S,6R)-3-benzyloxy-6-benzyloxymethyl-5-hydroxy-2-(4-methoxy-phenoxy)-tetrahydro-pyran-4-yloxy]-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl ester
• CAS No.: 159922-52-8
• Molecular Formula: C₇₃H₇₇NO₁₅
• Molecular Weight: 1208.41

Synonyms:(2S,4S,5R,6R)-5-Acetylamino-4-benzyloxy-2-[(2S,3R,4S,5S,6R)-3-benzyloxy-6-benzyloxymethyl-5-hydroxy-2-(4-methoxy-phenoxy)-tetrahydro-pyran-4-yloxy]-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl ester

Chemical Property of (2S,4S,5R,6R)-5-Acetylamino-4-benzyloxy-2-[(2S,3R,4S,5S,6R)-3-benzyloxy-6-benzyloxymethyl-5-hydroxy-2-(4-methoxy-phenoxy)-tetrahydro-pyran-4-yloxy]-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl ester

Chemical Property:

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Technology Process of (2S,4S,5R,6R)-5-Acetylamino-4-benzyloxy-2-[(2S,3R,4S,5S,6R)-3-benzyloxy-6-benzyloxymethyl-5-hydroxy-2-(4-methoxy-phenoxy)-tetrahydro-pyran-4-yloxy]-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl ester

There total 7 articles about (2S,4S,5R,6R)-5-Acetylamino-4-benzyloxy-2-[(2S,3R,4S,5S,6R)-3-benzyloxy-6-benzyloxymethyl-5-hydroxy-2-(4-methoxy-phenoxy)-tetrahydro-pyran-4-yloxy]-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl 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: 64.0%

C79H81NO15S (159922-51-7) → C66H69NO14 (159922-53-9) + (2S,4S,5R,6R)-5-Acetylamino-4-benzyloxy-2-[(2S,3R,4S,5S,6R)-3-benzyloxy-6-benzyloxymethyl-5-hydroxy-2-(4-methoxy-phenoxy)-tetrahydro-pyran-4-yloxy]-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl ester (159922-52-8)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); triphenylstannane; In benzene; for 6h; Heating;

DOI:10.1016/S0040-4039(00)76897-3

Reference yield:

benzyl bromide (100-39-0) → (2S,4S,5R,6R)-5-Acetylamino-4-benzyloxy-2-[(2S,3R,4S,5S,6R)-3-benzyloxy-6-benzyloxymethyl-5-hydroxy-2-(4-methoxy-phenoxy)-tetrahydro-pyran-4-yloxy]-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl ester (159922-52-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / NaH / tetrahydrofuran / 20 h / 60 °C

2: 95 percent / 80percent CF₃CO₂H, water / CH₂Cl₂ / 2 h / 0 °C

3: 69 percent / mercury salt

4: 64 percent / Ph₃SnH, AIBN / benzene / 6 h / Heating

With 2,2'-azobis(isobutyronitrile); mercury salt; triphenylstannane; water; sodium hydride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; benzene;

DOI:10.1016/S0040-4039(00)76897-3

Reference yield:

(3S,4R,5S,6R)-5-Acetylamino-4-benzyloxy-2-bromo-3-phenylsulfanyl-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl ester (132294-62-3) → (2S,4S,5R,6R)-5-Acetylamino-4-benzyloxy-2-[(2S,3R,4S,5S,6R)-3-benzyloxy-6-benzyloxymethyl-5-hydroxy-2-(4-methoxy-phenoxy)-tetrahydro-pyran-4-yloxy]-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl ester (159922-52-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 69 percent / mercury salt

2: 64 percent / Ph₃SnH, AIBN / benzene / 6 h / Heating

With 2,2'-azobis(isobutyronitrile); mercury salt; triphenylstannane; In benzene;

DOI:10.1016/S0040-4039(00)76897-3

upstream raw materials:

C₇₉H₈₁NO₁₅S

benzyl bromide

(3S,4R,5S,6R)-5-Acetylamino-4-benzyloxy-2-bromo-3-phenylsulfanyl-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl ester

4-methoxyphenyl 3,4-O-isopropylidene-β-D-galactopyranoside

Downstream raw materials:

C₂₄H₃₃NO₁₄

C₆₆H₆₉NO₁₄

(2S,4S,5R,6R)-5-Acetylamino-2-[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-hydroxymethyl-6-(4-methoxy-phenoxy)-tetrahydro-pyran-4-yloxy]-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid

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