2-(trimethylsilyl)ethyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->4)-2-O-benzoyl-6,7-di-O-benzyl-3-O-(p-methoxybenzyl)-L-glycero-α-D-manno-heptopyranoside

Base Information

Chemical Name:2-(trimethylsilyl)ethyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->4)-2-O-benzoyl-6,7-di-O-benzyl-3-O-(p-methoxybenzyl)-L-glycero-α-D-manno-heptopyranoside
CAS No.:623114-88-5
Molecular Formula:C₅₅H₆₈O₁₈Si
Molecular Weight:1045.22
Hs Code.:

2-(trimethylsilyl)ethyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->4)-2-O-benzoyl-6,7-di-O-benzyl-3-O-(p-methoxybenzyl)-L-glycero-α-D-manno-heptopyranoside

Synonyms:2-(trimethylsilyl)ethyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->4)-2-O-benzoyl-6,7-di-O-benzyl-3-O-(p-methoxybenzyl)-L-glycero-α-D-manno-heptopyranoside

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Chemical Property of 2-(trimethylsilyl)ethyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->4)-2-O-benzoyl-6,7-di-O-benzyl-3-O-(p-methoxybenzyl)-L-glycero-α-D-manno-heptopyranoside

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Technology Process of 2-(trimethylsilyl)ethyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->4)-2-O-benzoyl-6,7-di-O-benzyl-3-O-(p-methoxybenzyl)-L-glycero-α-D-manno-heptopyranoside

There total 15 articles about 2-(trimethylsilyl)ethyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->4)-2-O-benzoyl-6,7-di-O-benzyl-3-O-(p-methoxybenzyl)-L-glycero-α-D-manno-heptopyranoside 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: 94.0%

: 98-88-4
benzoyl chloride

: 623114-87-4
2-(trimethylsilyl)ethyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->4)-6,7-di-O-benzyl-3-O-(p-methoxybenzyl)-L-glycero-α-D-manno-heptopyranoside

: 623114-88-5
2-(trimethylsilyl)ethyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->4)-2-O-benzoyl-6,7-di-O-benzyl-3-O-(p-methoxybenzyl)-L-glycero-α-D-manno-heptopyranoside

Guidance literature:: With pyridine; at 20 ℃; for 8h;
DOI:10.1002/ejoc.200300309

Reference yield:

: 14218-11-2
2,3,4,6-tetra-O-benzoylglucosyl bromide

: 623114-88-5
2-(trimethylsilyl)ethyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->4)-2-O-benzoyl-6,7-di-O-benzyl-3-O-(p-methoxybenzyl)-L-glycero-α-D-manno-heptopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: 89 percent / 2,4,6-trimethylpyridine; AgOTf / CH₂Cl₂ / 24 h / 0 °C

2.1: 98 percent / NaOMe; MeOH / 24 h / 20 °C / pH 12

3.1: 99 percent / pyridine / 24 h / 20 °C

4.1: 96 percent / AcOH; H₂O / 24 h / 50 °C

5.1: dibutyltin oxide / benzene / 12 h / Heating

5.2: 74 percent / tetrabutylammonium bromide / benzene / 6 h / Heating

6.1: 94 percent / pyridine / 8 h / 20 °C

With pyridine; 2,4,6-trimethyl-pyridine; methanol; water; sodium methylate; silver trifluoromethanesulfonate; di(n-butyl)tin oxide; acetic acid; In dichloromethane; benzene; 2.1: Zemplen transesterification;
DOI:10.1002/ejoc.200300309

Reference yield:

: (3aS,4S,6S,7S,7aS)-7-(4-Methoxy-benzyloxy)-2,2-dimethyl-4-(2-trimethylsilanyl-ethoxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carbaldehyde

: 623114-88-5
2-(trimethylsilyl)ethyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->4)-2-O-benzoyl-6,7-di-O-benzyl-3-O-(p-methoxybenzyl)-L-glycero-α-D-manno-heptopyranoside

Guidance literature:: Multi-step reaction with 12 steps

1.1: 820 mg / tetrahydrofuran / 24 h / -60 °C

2.1: NaH / dimethylformamide / 0.5 h / 0 °C

2.2: 96 percent / dimethylformamide / 2 h / 20 °C

3.1: OsO₄; NaIO₄ / H₂O; 2-methyl-propan-2-ol; diethyl ether / 24 h / 20 °C

4.1: 640 mg / NaBH₄ / methanol; H₂O / 1 h / 20 °C

5.1: NaH / dimethylformamide / 0.5 h / 0 °C

5.2: 97 percent / dimethylformamide / 2 h / 20 °C

6.1: 93 percent / DDQ / CH₂Cl₂; H₂O / 1.5 h / 20 °C

7.1: 89 percent / 2,4,6-trimethylpyridine; AgOTf / CH₂Cl₂ / 24 h / 0 °C

8.1: 98 percent / NaOMe; MeOH / 24 h / 20 °C / pH 12

9.1: 99 percent / pyridine / 24 h / 20 °C

10.1: 96 percent / AcOH; H₂O / 24 h / 50 °C

11.1: dibutyltin oxide / benzene / 12 h / Heating

11.2: 74 percent / tetrabutylammonium bromide / benzene / 6 h / Heating

12.1: 94 percent / pyridine / 8 h / 20 °C

With pyridine; 2,4,6-trimethyl-pyridine; methanol; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; water; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; di(n-butyl)tin oxide; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; benzene; 8.1: Zemplen transesterification;
DOI:10.1002/ejoc.200300309