5-amino-2,6-anhydro-3,4-bis(O-tert-butyldimethylsilyl)-7-O-(4-methoxybenzyl)-5-deoxy-D-glycero-D-gulo-heptonic acid

Base Information

Chemical Name:5-amino-2,6-anhydro-3,4-bis(O-tert-butyldimethylsilyl)-7-O-(4-methoxybenzyl)-5-deoxy-D-glycero-D-gulo-heptonic acid
CAS No.:944072-38-2
Molecular Formula:C₂₇H₄₉NO₇Si₂
Molecular Weight:555.86
Hs Code.:

Synonyms:5-amino-2,6-anhydro-3,4-bis(O-tert-butyldimethylsilyl)-7-O-(4-methoxybenzyl)-5-deoxy-D-glycero-D-gulo-heptonic acid

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Chemical Property of 5-amino-2,6-anhydro-3,4-bis(O-tert-butyldimethylsilyl)-7-O-(4-methoxybenzyl)-5-deoxy-D-glycero-D-gulo-heptonic acid

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Technology Process of 5-amino-2,6-anhydro-3,4-bis(O-tert-butyldimethylsilyl)-7-O-(4-methoxybenzyl)-5-deoxy-D-glycero-D-gulo-heptonic acid

There total 9 articles about 5-amino-2,6-anhydro-3,4-bis(O-tert-butyldimethylsilyl)-7-O-(4-methoxybenzyl)-5-deoxy-D-glycero-D-gulo-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:

: C₂₈H₅₁O₇NSi₂

: 944072-38-2
5-amino-2,6-anhydro-3,4-bis(O-tert-butyldimethylsilyl)-7-O-(4-methoxybenzyl)-5-deoxy-D-glycero-D-gulo-heptonic acid

Guidance literature:: With lithium hydroxide; water; In tetrahydrofuran; at 50 ℃; for 2h;
DOI:10.1055/s-2007-965942

Reference yield:

: methyl 2,6-anhydro-5,7-O-(4-methoxybenzylidene)-D-glycero-L-manno-heptonate

: 944072-38-2
5-amino-2,6-anhydro-3,4-bis(O-tert-butyldimethylsilyl)-7-O-(4-methoxybenzyl)-5-deoxy-D-glycero-D-gulo-heptonic acid

Guidance literature:: Multi-step reaction with 6 steps

1: 80 percent / imidazole; DMAP / dimethylformamide / 24 h / 65 °C

2: 64 percent / sodium cyanoborohydride; 4 Angstroem MS; TFA / tetrahydrofuran; CH₂Cl₂ / 24 h / 20 °C

3: 87 percent / pyridine; DMAP / CH₂Cl₂ / 35 h / 20 °C

4: 89 percent / NaN₃ / dimethylformamide / 2.5 h / 20 °C

5: PPh₃; H₂O / tetrahydrofuran / 2 h / 20 - 50 °C

6: 12.9 mg / lithium hydroxide; H₂O / tetrahydrofuran / 2 h / 50 °C

With pyridine; 1H-imidazole; dmap; lithium hydroxide; sodium azide; 4 Angstroem MS; water; sodium cyanoborohydride; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 5: Staudinger reaction;
DOI:10.1055/s-2007-965942

Reference yield:

: 944072-37-1
methyl 2,6-anhydro-5-azido-3,4-bis(O-tert-butyldimethylsilyl)-7-O-(4-methoxybenzyl)-5-deoxy-D-glycero-D-gulo-heptonate

: 944072-38-2
5-amino-2,6-anhydro-3,4-bis(O-tert-butyldimethylsilyl)-7-O-(4-methoxybenzyl)-5-deoxy-D-glycero-D-gulo-heptonic acid

Guidance literature:: Multi-step reaction with 2 steps

1: PPh₃; H₂O / tetrahydrofuran / 2 h / 20 - 50 °C

2: 12.9 mg / lithium hydroxide; H₂O / tetrahydrofuran / 2 h / 50 °C

With lithium hydroxide; water; triphenylphosphine; In tetrahydrofuran; 1: Staudinger reaction;
DOI:10.1055/s-2007-965942