2-(trimethylsilyl)ethyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->4)-6,7-di-O-benzyl-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)-6,7-di-O-benzyl-L-glycero-α-D-manno-heptopyranoside
CAS No.:623114-86-3
Molecular Formula:C₄₀H₅₆O₁₆Si
Molecular Weight:820.961
Hs Code.:

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

There total 16 articles about 2-(trimethylsilyl)ethyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->4)-6,7-di-O-benzyl-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: 96.0%

: 623114-85-2
2-(trimethylsilyl)ethyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->4)-6,7-di-O-benzyl-2,3-O-isopropylidene-L-glycero-α-D-manno-heptopyranoside

: 623114-86-3
2-(trimethylsilyl)ethyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->4)-6,7-di-O-benzyl-L-glycero-α-D-manno-heptopyranoside

Guidance literature:: With water; acetic acid; at 50 ℃; for 24h;
DOI:10.1002/ejoc.200300309

Reference yield:

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

: 623114-86-3
2-(trimethylsilyl)ethyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->4)-6,7-di-O-benzyl-L-glycero-α-D-manno-heptopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 89 percent / 2,4,6-trimethylpyridine; AgOTf / CH₂Cl₂ / 24 h / 0 °C

2: 98 percent / NaOMe; MeOH / 24 h / 20 °C / pH 12

3: 99 percent / pyridine / 24 h / 20 °C

4: 96 percent / AcOH; H₂O / 24 h / 50 °C

With pyridine; 2,4,6-trimethyl-pyridine; methanol; water; sodium methylate; silver trifluoromethanesulfonate; acetic acid; In dichloromethane; 2: Zemplen transesterification;
DOI:10.1002/ejoc.200300309

Reference yield:

: 81336-89-2
2-(trimethylsilyl)ethyl α-D-mannopyranoside

: 623114-86-3
2-(trimethylsilyl)ethyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->4)-6,7-di-O-benzyl-L-glycero-α-D-manno-heptopyranoside

Guidance literature:: Multi-step reaction with 15 steps

1.1: 89 percent / DMAP; pyridine / 24 h / 40 °C

2.1: 87 percent / p-toluenesulfonic acid monohydrate / 0.75 h / 20 °C

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

3.2: 95 percent / dimethylformamide / 2 h / 20 °C

4.1: 61 percent / AcOH / 11 h / 60 °C

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

6.1: 820 mg / tetrahydrofuran / 24 h / -60 °C

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

7.2: 96 percent / dimethylformamide / 2 h / 20 °C

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

9.1: 640 mg / NaBH₄ / methanol; H₂O / 1 h / 20 °C

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

10.2: 97 percent / dimethylformamide / 2 h / 20 °C

11.1: 93 percent / DDQ / CH₂Cl₂; H₂O / 1.5 h / 20 °C

12.1: 89 percent / 2,4,6-trimethylpyridine; AgOTf / CH₂Cl₂ / 24 h / 0 °C

13.1: 98 percent / NaOMe; MeOH / 24 h / 20 °C / pH 12

14.1: 99 percent / pyridine / 24 h / 20 °C

15.1: 96 percent / AcOH; H₂O / 24 h / 50 °C

With pyridine; 2,4,6-trimethyl-pyridine; methanol; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; oxalyl dichloride; water; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; toluene-4-sulfonic acid; acetic acid; 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; 5.1: Swern oxidation / 13.1: Zemplen transesterification;
DOI:10.1002/ejoc.200300309