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

Base Information

Chemical Name: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
CAS No.:870529-05-8
Molecular Formula:C₃₀H₄₁NO₁₀
Molecular Weight:575.656
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 6 articles about 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 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: 58.6%

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

: 2217-02-9
(1R)-endo-(+)-fenchol

: 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

Guidance literature:: 2-(acetoxymethyl)-5-{[(benzyloxy)carbonyl]amino}tetrahydropyran-3,4,6-triyl triacetate; (1R)-endo-(+)-fenchol; With calcium sulfate; In dichloromethane; at 20 ℃; for 0.5h;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; for 0.75h;
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

: 870529-05-8
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

Guidance literature:: Multi-step reaction with 3 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

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

Reference yield:

: 51471-40-0
2--2-deoxy-D-glucopyranose

: 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

Guidance literature:: Multi-step reaction with 4 steps

1.1: 72 percent / pyridine / 20 °C

2.1: 100 percent / HCl / acetone

3.1: 83 percent / NaHCO₃ / CHCl₃; H₂O / pH 8.0

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

4.2: 58.6 percent / TMSOTf / CH₂Cl₂ / 0.75 h

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