3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-glycero-L-gluco-heptonic acid

Base Information

Chemical Name:3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-glycero-L-gluco-heptonic acid
CAS No.:201864-30-4
Molecular Formula:C₃₀H₃₃NO₇
Molecular Weight:519.595
Hs Code.:

Synonyms:3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-glycero-L-gluco-heptonic acid

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Chemical Property of 3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-glycero-L-gluco-heptonic acid

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Technology Process of 3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-glycero-L-gluco-heptonic acid

There total 4 articles about 3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-glycero-L-gluco-heptonic acid 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: 86.0%

: 124-38-9,18923-20-1
carbon dioxide

: 201864-27-9
N-((2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-chloro-tetrahydro-pyran-3-yl)-acetamide

: 201864-30-4
3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-glycero-L-gluco-heptonic acid

Guidance literature:: With n-butyllithium; naphthalen-1-yl-lithium; In tetrahydrofuran; at -90 ℃; 1.) 1 min; 2.) 11 min;
DOI:10.1016/S0040-4039(97)10567-6

Reference yield:

: 4171-72-6,4171-79-3,121123-45-3
2-acetamido-2-deoxy-3,4,6-tri-O-benzyl-D-galactopyranose

: 201864-30-4
3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-glycero-L-gluco-heptonic acid

Guidance literature:: Multi-step reaction with 2 steps

1: SOCl₂ / toluene; CHCl₃ / 0.5 h

2: 1.24 g / BuLi; lithium naphthalenide / tetrahydrofuran / 1 h / -78 °C

With n-butyllithium; thionyl chloride; naphthalen-1-yl-lithium; In tetrahydrofuran; chloroform; toluene; 1: Substitution / 2: Carboxylation;
DOI:10.1021/jo990766l

Reference yield:

: 79781-69-4
2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-galactopyranose

: 201864-30-4
3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-glycero-L-gluco-heptonic acid

Guidance literature:: Multi-step reaction with 4 steps

1: hydrogenolysis

3: SOCl₂ / CHCl₃; toluene / 0.33 h / Ambient temperature

4: 86 percent / 1.) n-BuLi; 2.) lithium naphthalenide (LN) / tetrahydrofuran / -90 °C / 1.) 1 min; 2.) 11 min

With n-butyllithium; thionyl chloride; naphthalen-1-yl-lithium; In tetrahydrofuran; chloroform; toluene;
DOI:10.1016/S0040-4039(97)10567-6