(2R,3R,4R,5S,6R)-5-Acetylamino-4-benzyloxy-3-phenylselanyl-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2R,3R,4R,5S,6R)-5-Acetylamino-4-benzyloxy-3-phenylselanyl-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS No.: 116096-69-6
• Molecular Formula: C₅₈H₆₇NO₁₄Se
• Molecular Weight: 1081.13
• Mol file: 116096-69-6.mol

Synonyms:(2R,3R,4R,5S,6R)-5-Acetylamino-4-benzyloxy-3-phenylselanyl-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property of (2R,3R,4R,5S,6R)-5-Acetylamino-4-benzyloxy-3-phenylselanyl-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,5S,6R)-5-Acetylamino-4-benzyloxy-3-phenylselanyl-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 13 articles about (2R,3R,4R,5S,6R)-5-Acetylamino-4-benzyloxy-3-phenylselanyl-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-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: 82.0%

methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3,5-trideoxy-2-fluoro-3-(phenylseleno)-D-erythro-β-L-manno-2-nonulopyranosonate (116180-63-3) + 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (4064-06-6) → (2R,3R,4R,5S,6R)-5-Acetylamino-4-benzyloxy-3-phenylselanyl-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (116096-69-6)

Guidance literature:

With silver trifluoromethanesulfonate; tin(ll) chloride; In 1,2-dichloro-ethane; -15 deg C, 30 min, then 0 deg C, 30 min, then room temp., 1h;

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

Reference yield: 42.0%

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) + 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (4064-06-6) → methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate (116096-63-0) + (2R,3R,4R,5S,6R)-5-Acetylamino-4-benzyloxy-3-phenylselanyl-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (116096-69-6) + O--(2->6)-1,2;3,4-di-O-isopropylidene-α-D-galactopyranose (116096-68-5)

Guidance literature:

With 4 A molecular sieve; tributylstannyl trifluoromethanesulfonate; In tetrachloromethane; for 16h; Ambient temperature;

DOI:10.1016/S0040-4039(00)61852-X

Reference yield:

Phenylselenyl chloride (5707-04-0) → (2R,3R,4R,5S,6R)-5-Acetylamino-4-benzyloxy-3-phenylselanyl-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (116096-69-6)

Guidance literature:

Multi-step reaction with 4 steps

2: 11 percent / trimethylsilyl triflate / 1,2-dichloro-ethane / 0.5 h / 0 °C

3: 70 percent / diethylaminosulfur trifluoride / tetrahydrofuran / -20 °C

4: 82 percent / molecular sieves 4 A, silver triflate, SnCl₂ / 1,2-dichloro-ethane / 1 h / Ambient temperature

With diethylamino-sulfur trifluoride; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; silver trifluoromethanesulfonate; tin(ll) chloride; In tetrahydrofuran; 1,2-dichloro-ethane;

DOI:10.1016/S0040-4039(00)61852-X

upstream raw materials:

methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3,5-trideoxy-2-fluoro-3-(phenylseleno)-D-erythro-β-L-manno-2-nonulopyranosonate

1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3,5-trideoxy-2-fluoro-3-phenylseleno-D-erythro-α-L-gluco-nonulopyranosate

Phenylselenyl chloride