2-(4',6'-O-isopropylidene-α-D-mannopyranosyl)-2-benzamido-(2R)-propionic acid 1,2'-lactone

Base Information

Chemical Name:2-(4',6'-O-isopropylidene-α-D-mannopyranosyl)-2-benzamido-(2R)-propionic acid 1,2'-lactone
CAS No.:500757-04-0
Molecular Formula:C₁₉H₂₃NO₇
Molecular Weight:377.394
Hs Code.:

Synonyms:2-(4',6'-O-isopropylidene-α-D-mannopyranosyl)-2-benzamido-(2R)-propionic acid 1,2'-lactone

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Chemical Property of 2-(4',6'-O-isopropylidene-α-D-mannopyranosyl)-2-benzamido-(2R)-propionic acid 1,2'-lactone

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Technology Process of 2-(4',6'-O-isopropylidene-α-D-mannopyranosyl)-2-benzamido-(2R)-propionic acid 1,2'-lactone

There total 4 articles about 2-(4',6'-O-isopropylidene-α-D-mannopyranosyl)-2-benzamido-(2R)-propionic acid 1,2'-lactone 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: 98.0%

: (4R)-4-methyl-4-(4',6'-O-isopropylidene-2',3'-dideoxy-α-D-erythro-2'-hexenopyranosyl)-2-phenyl-5(4H)-oxazolone

: 500757-04-0
2-(4',6'-O-isopropylidene-α-D-mannopyranosyl)-2-benzamido-(2R)-propionic acid 1,2'-lactone

Guidance literature:: With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; acetone; tert-butyl alcohol; at 20 ℃; for 24h;
DOI:10.1016/S0040-4020(02)01225-5

Reference yield:

: 2198-64-3,1205-02-3,90988-29-7
N-Benzoylalanine

: 500757-04-0
2-(4',6'-O-isopropylidene-α-D-mannopyranosyl)-2-benzamido-(2R)-propionic acid 1,2'-lactone

Guidance literature:: Multi-step reaction with 3 steps

1: 80 percent / DMAP; DMAP hydrochloride; DCC / CHCl₃ / 9 h / Heating

2: 62 percent / triethylamine; triphenylphosphine / CCl₄ / 12 h / 20 °C

3: 98 percent / 4-methylmorpholine N-oxide; OsO₄ / acetone; H₂O; 2-methyl-propan-2-ol / 24 h / 20 °C

With dmap; osmium(VIII) oxide; 4-(dimethylamino)pyridine hydrochloride; 4-methylmorpholine N-oxide; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; In tetrachloromethane; chloroform; water; acetone; tert-butyl alcohol; 2: Claisen rearrangement;
DOI:10.1016/S0040-4020(02)01225-5

Reference yield:

: 329027-49-8
1,5-anhydro-4,6-O-isopropylidene-2-deoxy-D-ribo-hex-1-enitol

: 500757-04-0
2-(4',6'-O-isopropylidene-α-D-mannopyranosyl)-2-benzamido-(2R)-propionic acid 1,2'-lactone

Guidance literature:: Multi-step reaction with 3 steps

1: 80 percent / DMAP; DMAP hydrochloride; DCC / CHCl₃ / 9 h / Heating

2: 62 percent / triethylamine; triphenylphosphine / CCl₄ / 12 h / 20 °C

3: 98 percent / 4-methylmorpholine N-oxide; OsO₄ / acetone; H₂O; 2-methyl-propan-2-ol / 24 h / 20 °C

With dmap; osmium(VIII) oxide; 4-(dimethylamino)pyridine hydrochloride; 4-methylmorpholine N-oxide; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; In tetrachloromethane; chloroform; water; acetone; tert-butyl alcohol; 2: Claisen rearrangement;
DOI:10.1016/S0040-4020(02)01225-5