3,4,6-tri-O-benzyl-2-carboxy-2-deoxy-α-D-galactohexopyranosylaminolactam

Base Information

• Chemical Name: 3,4,6-tri-O-benzyl-2-carboxy-2-deoxy-α-D-galactohexopyranosylaminolactam
• CAS No.: 121250-72-4
• Molecular Formula: C₂₈H₂₉NO₅
• Molecular Weight: 459.542
• Mol file: 121250-72-4.mol

Synonyms:3,4,6-tri-O-benzyl-2-carboxy-2-deoxy-α-D-galactohexopyranosylaminolactam

Chemical Property of 3,4,6-tri-O-benzyl-2-carboxy-2-deoxy-α-D-galactohexopyranosylaminolactam

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,4,6-tri-O-benzyl-2-carboxy-2-deoxy-α-D-galactohexopyranosylaminolactam

There total 4 articles about 3,4,6-tri-O-benzyl-2-carboxy-2-deoxy-α-D-galactohexopyranosylaminolactam 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: 49.0%

isocyanate de chlorosulfonyle (1189-71-5) + 3,4,6-tri-O-benzyl-D-galactal (80040-79-5) → 3,4,6-tri-O-benzyl-2-carboxy-2-deoxy-α-D-galactohexopyranosylaminolactam (121250-72-4)

Guidance literature:

With sodium carbonate; In toluene; at -78 - -62 ℃; for 3h; Autoclave; Inert atmosphere;

DOI:10.15227/orgsyn.098.0491

Reference yield:

benzyl bromide (100-39-0) → 3,4,6-tri-O-benzyl-2-carboxy-2-deoxy-α-D-galactohexopyranosylaminolactam (121250-72-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) sodium methoxide; 2.) KOH / 1.) MeOH; 2.) DMSO

2: 1.) acetonitrile, 16 deg C, 2 h; 2.) acetonitrile, -30 -> r.t.

With potassium hydroxide; sodium methylate;

DOI:10.1016/0040-4020(89)80050-X

Reference yield:

triacetyl-D-galactal (4098-06-0) → 3,4,6-tri-O-benzyl-2-carboxy-2-deoxy-α-D-galactohexopyranosylaminolactam (121250-72-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) sodium methoxide; 2.) KOH / 1.) MeOH; 2.) DMSO

2: 1.) acetonitrile, 16 deg C, 2 h; 2.) acetonitrile, -30 -> r.t.

With potassium hydroxide; sodium methylate;

DOI:10.1016/0040-4020(89)80050-X

upstream raw materials:

3,4,6-tri-O-benzyl-D-galactal

Trichloroacetyl isocyanate

benzyl bromide

triacetyl-D-galactal

Downstream raw materials:

N-benzyl-2-carboxy-2-deoxy-2-hydroxymethyl-α-D-ribopentofuranosylaminolactam

(1R,4S,6R,10S)-3-Benzyl-9,10-dihydroxy-5,8-dioxa-3-aza-tricyclo[4.3.1.0^1,4]decan-2-one

N-benzyl-2-carboxy-2-deoxy-α-D-galactohexopyranosylaminolactam

(3R,4S,1'R) 1-t-butyldimethylsilyl-3-diphenylmethoxycarbonyl-4-(1'-diphenylmethoxycarbonyl-2'-hydroxy)ethoxy-azetidinone-2