2-(trimethylsilyl)ethyl 7,8-dideoxy-2,3-O-isopropylidene-4-O-(p-methoxybenzyl)-L-glycero-α-D-manno-oct-7-enopyranoside

Base Information

Chemical Name:2-(trimethylsilyl)ethyl 7,8-dideoxy-2,3-O-isopropylidene-4-O-(p-methoxybenzyl)-L-glycero-α-D-manno-oct-7-enopyranoside
CAS No.:623114-71-6
Molecular Formula:C₂₄H₃₈O₇Si
Molecular Weight:466.647
Hs Code.:

Synonyms:2-(trimethylsilyl)ethyl 7,8-dideoxy-2,3-O-isopropylidene-4-O-(p-methoxybenzyl)-L-glycero-α-D-manno-oct-7-enopyranoside

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Chemical Property of 2-(trimethylsilyl)ethyl 7,8-dideoxy-2,3-O-isopropylidene-4-O-(p-methoxybenzyl)-L-glycero-α-D-manno-oct-7-enopyranoside

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Technology Process of 2-(trimethylsilyl)ethyl 7,8-dideoxy-2,3-O-isopropylidene-4-O-(p-methoxybenzyl)-L-glycero-α-D-manno-oct-7-enopyranoside

There total 3 articles about 2-(trimethylsilyl)ethyl 7,8-dideoxy-2,3-O-isopropylidene-4-O-(p-methoxybenzyl)-L-glycero-α-D-manno-oct-7-enopyranoside 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:

: 623114-70-5
2-(trimethylsilyl)ethyl 2,3-O-isopropylidene-4-O-(p-methoxybenzyl)-α-D-mannopyranoside

: 623114-71-6
2-(trimethylsilyl)ethyl 7,8-dideoxy-2,3-O-isopropylidene-4-O-(p-methoxybenzyl)-L-glycero-α-D-manno-oct-7-enopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: oxalyl chloride; DMSO; Et₃N / tetrahydrofuran / 0.25 h / -60 °C

2: 820 mg / tetrahydrofuran / 24 h / -60 °C

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; 1: Swern oxidation;
DOI:10.1002/ejoc.200300309

Reference yield:

: 623114-67-0
2-(trimethylsilyl)ethyl 6-O-trityl-α-D-mannopyranoside

: 623114-71-6
2-(trimethylsilyl)ethyl 7,8-dideoxy-2,3-O-isopropylidene-4-O-(p-methoxybenzyl)-L-glycero-α-D-manno-oct-7-enopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: 87 percent / p-toluenesulfonic acid monohydrate / 0.75 h / 20 °C

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

2.2: 95 percent / dimethylformamide / 2 h / 20 °C

3.1: 61 percent / AcOH / 11 h / 60 °C

4.1: oxalyl chloride; DMSO; Et₃N / tetrahydrofuran / 0.25 h / -60 °C

5.1: 820 mg / tetrahydrofuran / 24 h / -60 °C

With oxalyl dichloride; sodium hydride; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide; 4.1: Swern oxidation;
DOI:10.1002/ejoc.200300309