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

Base Information

• Chemical Name: (2S,3S,4R,5S,6R)-5-Acetylamino-4-benzyloxy-2-chloro-3-phenylsulfanyl-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS No.: 128705-82-8
• Molecular Formula: C₄₆H₄₈ClNO₈S
• Molecular Weight: 810.408

Synonyms:(2S,3S,4R,5S,6R)-5-Acetylamino-4-benzyloxy-2-chloro-3-phenylsulfanyl-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property of (2S,3S,4R,5S,6R)-5-Acetylamino-4-benzyloxy-2-chloro-3-phenylsulfanyl-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property:

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Safty Information:

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Technology Process of (2S,3S,4R,5S,6R)-5-Acetylamino-4-benzyloxy-2-chloro-3-phenylsulfanyl-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 13 articles about (2S,3S,4R,5S,6R)-5-Acetylamino-4-benzyloxy-2-chloro-3-phenylsulfanyl-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-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: 99.0%

methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-3-phenylthio-D-erythro-β-L-gluco-2-nonulopyranosonate (139684-71-2) → methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2-chloro-2,3,5-trideoxy-3-phenylthio-D-erythro-β-L-gluco-2-nonulopyranosonate (120308-52-3,128705-82-8)

Guidance literature:

With tetrachloromethane; Hexamethylphosphorous triamide; In tetrahydrofuran; -78 deg C -> room temp. (3h);

DOI:10.1016/S0040-4020(01)97586-6

Reference yield:

methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3,5-trideoxy-2-fluoro-3-phenylseleno-D-erythro-α-L-gluco-nonulopyranosate (116096-67-4,116180-63-3,125356-39-0,125356-40-3,128658-86-6) → methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2-chloro-2,3,5-trideoxy-3-phenylthio-D-erythro-β-L-gluco-2-nonulopyranosonate (120308-52-3,128705-82-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 19 percent / AgOSO₂CF₃, SnCl₂ / CCl₄ / molecular sieves; -20 deg, 30 min, then 0 deg C, 30 min, then room temp., 2h

2: 78 percent / N-bromosuccinimide / acetonitrile; H₂O / 0.5 h / 60 °C

3: 4.23 g / t-BuOK / 2-methyl-propan-2-ol; tetrahydrofuran / 0 deg C, 2h, then room temp., 1h

4: DBU / toluene / 0 deg C, 2h, then room temp., 30 min.

5: 99 percent / (Me₂N)3P, CCl₄ / tetrahydrofuran / -78 deg C -> room temp. (3h)

With tetrachloromethane; N-Bromosuccinimide; potassium tert-butylate; silver trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; tin(ll) chloride; Hexamethylphosphorous triamide; In tetrahydrofuran; tetrachloromethane; water; toluene; acetonitrile; tert-butyl alcohol;

DOI:10.1016/S0040-4020(01)97586-6

Reference yield:

methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-3-phenylseleno-D-erythro-β-L-gluco-2-nonulopyranosonate (125288-70-2,125288-71-3,128596-94-1) → methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2-chloro-2,3,5-trideoxy-3-phenylthio-D-erythro-β-L-gluco-2-nonulopyranosonate (120308-52-3,128705-82-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 88 percent / diethylaminosulfur trifluoride / toluene; 1,2-dichloro-ethane / -40 deg C, 3h, then room temp., 1h

2: 19 percent / AgOSO₂CF₃, SnCl₂ / CCl₄ / molecular sieves; -20 deg, 30 min, then 0 deg C, 30 min, then room temp., 2h

3: 78 percent / N-bromosuccinimide / acetonitrile; H₂O / 0.5 h / 60 °C

4: 4.23 g / t-BuOK / 2-methyl-propan-2-ol; tetrahydrofuran / 0 deg C, 2h, then room temp., 1h

5: DBU / toluene / 0 deg C, 2h, then room temp., 30 min.

6: 99 percent / (Me₂N)3P, CCl₄ / tetrahydrofuran / -78 deg C -> room temp. (3h)

With tetrachloromethane; N-Bromosuccinimide; diethylamino-sulfur trifluoride; potassium tert-butylate; silver trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; tin(ll) chloride; Hexamethylphosphorous triamide; In tetrahydrofuran; tetrachloromethane; water; 1,2-dichloro-ethane; toluene; acetonitrile; tert-butyl alcohol;

DOI:10.1016/S0040-4020(01)97586-6

upstream raw materials:

methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-3-phenylthio-D-erythro-β-L-gluco-2-nonulopyranosonate

5-acetamido-4,7,8,9-tetra-O-benzyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonic acid

methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate

methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-3-bromo-3,5-dideoxy-D-erythro-L-manno-2-nonulopyranosonate

Downstream raw materials:

C₁₀₀H₁₀₅NO₁₉S

benzyl O--(2->3)-O-(2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

benzyl O--(2->3)-O-(2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

methyl O--(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

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