2-(trimethylsilyl)ethyl 6-O-benzyl-2,3-O-isopropylidene-4-O-(p-methoxybenzyl)-L-glycero-α-D-manno-heptopyranoside

Base Information

Chemical Name:2-(trimethylsilyl)ethyl 6-O-benzyl-2,3-O-isopropylidene-4-O-(p-methoxybenzyl)-L-glycero-α-D-manno-heptopyranoside
CAS No.:623114-73-8
Molecular Formula:C₃₀H₄₄O₈Si
Molecular Weight:560.76
Hs Code.:

Synonyms:2-(trimethylsilyl)ethyl 6-O-benzyl-2,3-O-isopropylidene-4-O-(p-methoxybenzyl)-L-glycero-α-D-manno-heptopyranoside

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Chemical Property of 2-(trimethylsilyl)ethyl 6-O-benzyl-2,3-O-isopropylidene-4-O-(p-methoxybenzyl)-L-glycero-α-D-manno-heptopyranoside

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Technology Process of 2-(trimethylsilyl)ethyl 6-O-benzyl-2,3-O-isopropylidene-4-O-(p-methoxybenzyl)-L-glycero-α-D-manno-heptopyranoside

There total 6 articles about 2-(trimethylsilyl)ethyl 6-O-benzyl-2,3-O-isopropylidene-4-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:

: (R)-Benzyloxy-[(3aS,4S,6S,7R,7aS)-7-(4-methoxy-benzyloxy)-2,2-dimethyl-4-(2-trimethylsilanyl-ethoxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl]-acetaldehyde

: 623114-73-8
2-(trimethylsilyl)ethyl 6-O-benzyl-2,3-O-isopropylidene-4-O-(p-methoxybenzyl)-L-glycero-α-D-manno-heptopyranoside

Guidance literature:: With sodium tetrahydroborate; In methanol; water; at 20 ℃; for 1h;
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

: 623114-73-8
2-(trimethylsilyl)ethyl 6-O-benzyl-2,3-O-isopropylidene-4-O-(p-methoxybenzyl)-L-glycero-α-D-manno-heptopyranoside

Guidance literature:: Multi-step reaction with 4 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

With sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; sodium hydride; In tetrahydrofuran; methanol; diethyl ether; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1002/ejoc.200300309

Reference yield:

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

: 623114-73-8
2-(trimethylsilyl)ethyl 6-O-benzyl-2,3-O-isopropylidene-4-O-(p-methoxybenzyl)-L-glycero-α-D-manno-heptopyranoside

Guidance literature:: Multi-step reaction with 5 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

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

5.1: 640 mg / NaBH₄ / methanol; H₂O / 1 h / 20 °C

With sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; diethyl ether; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Swern oxidation;
DOI:10.1002/ejoc.200300309