2-(trimethylsilyl)ethyl 6-O-benzyl-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 6-O-benzyl-7,8-dideoxy-2,3-O-isopropylidene-4-O-(p-methoxybenzyl)-L-glycero-α-D-manno-oct-7-enopyranoside
CAS No.:623114-72-7
Molecular Formula:C₃₁H₄₄O₇Si
Molecular Weight:556.772
Hs Code.:

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

There total 4 articles about 2-(trimethylsilyl)ethyl 6-O-benzyl-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: 96.0%

: 100-39-0
benzyl bromide

: 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

: 623114-72-7
2-(trimethylsilyl)ethyl 6-O-benzyl-7,8-dideoxy-2,3-O-isopropylidene-4-O-(p-methoxybenzyl)-L-glycero-α-D-manno-oct-7-enopyranoside

Guidance literature:: 2-(trimethylsilyl)ethyl 7,8-dideoxy-2,3-O-isopropylidene-4-O-(p-methoxybenzyl)-L-glycero-α-D-manno-oct-7-enopyranoside; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h;

benzyl bromide; In N,N-dimethyl-formamide; at 20 ℃; for 2h; Further stages.;
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

: 623114-72-7
2-(trimethylsilyl)ethyl 6-O-benzyl-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

1.1: 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

With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.200300309

Reference yield:

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

: 623114-72-7
2-(trimethylsilyl)ethyl 6-O-benzyl-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 3 steps

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

2.1: 820 mg / tetrahydrofuran / 24 h / -60 °C

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

3.2: 96 percent / dimethylformamide / 2 h / 20 °C

With oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide; 1.1: Swern oxidation;
DOI:10.1002/ejoc.200300309