2-(trimethylsilyl)ethyl 4,6,7-tri-O-benzyl-2,3-O-isopropylidene-L-glycero-α-D-manno-heptopyranoside

Base Information

Chemical Name:2-(trimethylsilyl)ethyl 4,6,7-tri-O-benzyl-2,3-O-isopropylidene-L-glycero-α-D-manno-heptopyranoside
CAS No.:623114-76-1
Molecular Formula:C₃₆H₄₈O₇Si
Molecular Weight:620.858
Hs Code.:

Synonyms:2-(trimethylsilyl)ethyl 4,6,7-tri-O-benzyl-2,3-O-isopropylidene-L-glycero-α-D-manno-heptopyranoside

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Chemical Property of 2-(trimethylsilyl)ethyl 4,6,7-tri-O-benzyl-2,3-O-isopropylidene-L-glycero-α-D-manno-heptopyranoside

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Technology Process of 2-(trimethylsilyl)ethyl 4,6,7-tri-O-benzyl-2,3-O-isopropylidene-L-glycero-α-D-manno-heptopyranoside

There total 11 articles about 2-(trimethylsilyl)ethyl 4,6,7-tri-O-benzyl-2,3-O-isopropylidene-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: 95.0%

: 100-39-0
benzyl bromide

: 623114-75-0
2-(trimethylsilyl)ethyl 6,7-di-O-benzyl-2,3-O-isopropylidene-L-glycero-α-D-manno-heptopyranoside

: 623114-76-1
2-(trimethylsilyl)ethyl 4,6,7-tri-O-benzyl-2,3-O-isopropylidene-L-glycero-α-D-manno-heptopyranoside

Guidance literature:: 2-(trimethylsilyl)ethyl 6,7-di-O-benzyl-2,3-O-isopropylidene-L-glycero-α-D-manno-heptopyranoside; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h;

benzyl bromide; In N,N-dimethyl-formamide; at 20 ℃; for 3h; 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

: 623114-76-1
2-(trimethylsilyl)ethyl 4,6,7-tri-O-benzyl-2,3-O-isopropylidene-L-glycero-α-D-manno-heptopyranoside

Guidance literature:: Multi-step reaction with 7 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: NaH / dimethylformamide / 0.5 h / 0 °C

7.2: 95 percent / dimethylformamide / 3 h / 20 °C

With sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 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

: 623114-76-1
2-(trimethylsilyl)ethyl 4,6,7-tri-O-benzyl-2,3-O-isopropylidene-L-glycero-α-D-manno-heptopyranoside

Guidance literature:: Multi-step reaction with 8 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

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

6.2: 97 percent / dimethylformamide / 2 h / 20 °C

7.1: 93 percent / DDQ / CH₂Cl₂; H₂O / 1.5 h / 20 °C

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

8.2: 95 percent / dimethylformamide / 3 h / 20 °C

With sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Swern oxidation;
DOI:10.1002/ejoc.200300309