phenyl 2,3-di-O-benzyl-4-O-(p-methoxybenzyl)-6-O-(p-nitrobenzoyl)-7-O-(tert-butyldiphenylsilyl)-L-glycero-α-D-thiomannoheptopyranoside

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Chemical Name:phenyl 2,3-di-O-benzyl-4-O-(p-methoxybenzyl)-6-O-(p-nitrobenzoyl)-7-O-(tert-butyldiphenylsilyl)-L-glycero-α-D-thiomannoheptopyranoside
CAS No.:850647-91-5
Molecular Formula:C₅₈H₅₉NO₁₀SSi
Molecular Weight:990.259
Hs Code.:

Synonyms:phenyl 2,3-di-O-benzyl-4-O-(p-methoxybenzyl)-6-O-(p-nitrobenzoyl)-7-O-(tert-butyldiphenylsilyl)-L-glycero-α-D-thiomannoheptopyranoside

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Chemical Property of phenyl 2,3-di-O-benzyl-4-O-(p-methoxybenzyl)-6-O-(p-nitrobenzoyl)-7-O-(tert-butyldiphenylsilyl)-L-glycero-α-D-thiomannoheptopyranoside

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Technology Process of phenyl 2,3-di-O-benzyl-4-O-(p-methoxybenzyl)-6-O-(p-nitrobenzoyl)-7-O-(tert-butyldiphenylsilyl)-L-glycero-α-D-thiomannoheptopyranoside

There total 8 articles about phenyl 2,3-di-O-benzyl-4-O-(p-methoxybenzyl)-6-O-(p-nitrobenzoyl)-7-O-(tert-butyldiphenylsilyl)-L-glycero-α-D-thiomannoheptopyranoside 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: 92.0%

: 850647-89-1
phenyl 2,3-di-O-benzyl-4-O-(p-methoxybenzyl)-D-glycero-α-D-thio-manno-heptopyranoside

: 58479-61-1
tert-butylchlorodiphenylsilane

: 62-23-7
4-nitro-benzoic acid

: 850647-91-5
phenyl 2,3-di-O-benzyl-4-O-(p-methoxybenzyl)-6-O-(p-nitrobenzoyl)-7-O-(tert-butyldiphenylsilyl)-L-glycero-α-D-thiomannoheptopyranoside

Guidance literature:: phenyl 2,3-di-O-benzyl-4-O-(p-methoxybenzyl)-D-glycero-α-D-thio-manno-heptopyranoside; tert-butylchlorodiphenylsilane; With 1H-imidazole; In dichloromethane; at 0 - 10 ℃; for 2h;

4-nitro-benzoic acid; With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 5h;
DOI:10.1021/ja061594u

Reference yield:

: 850647-86-8
phenyl 2,3-di-O-benzyl-4-O-(p-methoxybenzyl)-α-D-thiomannopyranoside

: 850647-91-5
phenyl 2,3-di-O-benzyl-4-O-(p-methoxybenzyl)-6-O-(p-nitrobenzoyl)-7-O-(tert-butyldiphenylsilyl)-L-glycero-α-D-thiomannoheptopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: oxalyl chloride; DMSO / CH₂Cl₂ / 1 h / -50 °C

1.2: 65 percent / nBuLi / tetrahydrofuran; hexane / 1 h / -40 °C

2.1: 61 percent / NMNO; OsO₄ / 2-methyl-propan-2-ol / 4 h / 20 °C

3.1: imidazole / CH₂Cl₂ / 2 h / 0 - 10 °C

3.2: 92 percent / PPh₃; DIAD / tetrahydrofuran / 5 h / 20 °C

With 1H-imidazole; osmium(VIII) oxide; oxalyl dichloride; bis-(2-chloro-ethyl)-methyl-amine oxide; dimethyl sulfoxide; In dichloromethane; tert-butyl alcohol;
DOI:10.1021/ja061594u

Reference yield:

: 850647-87-9
phenyl 2,3-di-O-benzyl-6,7-dideoxy-4-O-(p-methoxybenzyl)-α-D-thiohept-6-enopyranoside

: 850647-91-5
phenyl 2,3-di-O-benzyl-4-O-(p-methoxybenzyl)-6-O-(p-nitrobenzoyl)-7-O-(tert-butyldiphenylsilyl)-L-glycero-α-D-thiomannoheptopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: 61 percent / NMNO; OsO₄ / 2-methyl-propan-2-ol / 4 h / 20 °C

2.1: imidazole / CH₂Cl₂ / 2 h / 0 - 10 °C

2.2: 92 percent / PPh₃; DIAD / tetrahydrofuran / 5 h / 20 °C

With 1H-imidazole; osmium(VIII) oxide; bis-(2-chloro-ethyl)-methyl-amine oxide; In dichloromethane; tert-butyl alcohol;
DOI:10.1021/ja061594u