1,3,3-trimethylbicyclo[2.2.1]hept-2-yl 2-{[(benzyloxy)carbonyl]amino}-2-deoxy-β-D-glucopyranosiduronic acid

Base Information

Chemical Name:1,3,3-trimethylbicyclo[2.2.1]hept-2-yl 2-{[(benzyloxy)carbonyl]amino}-2-deoxy-β-D-glucopyranosiduronic acid
CAS No.:870529-12-7
Molecular Formula:C₂₄H₃₃NO₈
Molecular Weight:463.528
Hs Code.:

Synonyms:1,3,3-trimethylbicyclo[2.2.1]hept-2-yl 2-{[(benzyloxy)carbonyl]amino}-2-deoxy-β-D-glucopyranosiduronic acid

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Chemical Property of 1,3,3-trimethylbicyclo[2.2.1]hept-2-yl 2-{[(benzyloxy)carbonyl]amino}-2-deoxy-β-D-glucopyranosiduronic acid

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Technology Process of 1,3,3-trimethylbicyclo[2.2.1]hept-2-yl 2-{[(benzyloxy)carbonyl]amino}-2-deoxy-β-D-glucopyranosiduronic acid

There total 7 articles about 1,3,3-trimethylbicyclo[2.2.1]hept-2-yl 2-{[(benzyloxy)carbonyl]amino}-2-deoxy-β-D-glucopyranosiduronic 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: 53.0%

: 870529-05-8
1,3,3-trimethylbicyclo[2.2.1]hept-2-yl 3,4,6-tri-O-acetyl-2-{[(benzyloxy)carbonyl]amino}-2-deoxy-β-D-glucopyranoside

: 870529-12-7
1,3,3-trimethylbicyclo[2.2.1]hept-2-yl 2-{[(benzyloxy)carbonyl]amino}-2-deoxy-β-D-glucopyranosiduronic acid

Guidance literature:: 1,3,3-trimethylbicyclo[2.2.1]hept-2-yl 3,4,6-tri-O-acetyl-2-{[(benzyloxy)carbonyl]amino}-2-deoxy-β-D-glucopyranoside; With sodium; In methanol; at 20 ℃;

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium chlorite; sodium hydrogencarbonate; borax; In water; acetonitrile; for 0.5h; pH=9.0;
DOI:10.1002/hlca.200590175

Reference yield:

: 35946-66-8
2-(acetoxymethyl)-5-{[(benzyloxy)carbonyl]amino}tetrahydropyran-3,4,6-triyl triacetate

: 870529-12-7
1,3,3-trimethylbicyclo[2.2.1]hept-2-yl 2-{[(benzyloxy)carbonyl]amino}-2-deoxy-β-D-glucopyranosiduronic acid

Guidance literature:: Multi-step reaction with 2 steps

1.1: Drierite; 3A MS / CH₂Cl₂ / 0.5 h / 20 °C

1.2: 58.6 percent / TMSOTf / CH₂Cl₂ / 0.75 h

2.1: Na / methanol / 20 °C

2.2: 53 percent / TEMPO; NaClO₂; NaHCO₃ / Borax / acetonitrile; H₂O / 0.5 h / pH 9.0

With calcium sulfate; sodium; In methanol; dichloromethane;
DOI:10.1002/hlca.200590175

Reference yield:

: 114297-26-6
1,3,4,6-tetra-O-acetyl-2-deoxy-2-{[(4-methoxyphenyl)methylidene]amino}-D-glucopyranose

: 870529-12-7
1,3,3-trimethylbicyclo[2.2.1]hept-2-yl 2-{[(benzyloxy)carbonyl]amino}-2-deoxy-β-D-glucopyranosiduronic acid

Guidance literature:: Multi-step reaction with 4 steps

1.1: 100 percent / HCl / acetone

2.1: 83 percent / NaHCO₃ / CHCl₃; H₂O / pH 8.0

3.1: Drierite; 3A MS / CH₂Cl₂ / 0.5 h / 20 °C

3.2: 58.6 percent / TMSOTf / CH₂Cl₂ / 0.75 h

4.1: Na / methanol / 20 °C

4.2: 53 percent / TEMPO; NaClO₂; NaHCO₃ / Borax / acetonitrile; H₂O / 0.5 h / pH 9.0

With hydrogenchloride; calcium sulfate; sodium; sodium hydrogencarbonate; In methanol; dichloromethane; chloroform; water; acetone;
DOI:10.1002/hlca.200590175