(2-trimethylsilylethoxy)methyl 2,4,6,7,8-pentadeoxy-3-O-(4-methoxybenzyl)-2,4,6-tri-C-methyl-D-glycero-α-L-ido-7-octenopyranoside

Base Information

Chemical Name:(2-trimethylsilylethoxy)methyl 2,4,6,7,8-pentadeoxy-3-O-(4-methoxybenzyl)-2,4,6-tri-C-methyl-D-glycero-α-L-ido-7-octenopyranoside
CAS No.:158586-18-6
Molecular Formula:C₂₅H₄₂O₅Si
Molecular Weight:450.691
Hs Code.:

Synonyms:(2-trimethylsilylethoxy)methyl 2,4,6,7,8-pentadeoxy-3-O-(4-methoxybenzyl)-2,4,6-tri-C-methyl-D-glycero-α-L-ido-7-octenopyranoside

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Chemical Property of (2-trimethylsilylethoxy)methyl 2,4,6,7,8-pentadeoxy-3-O-(4-methoxybenzyl)-2,4,6-tri-C-methyl-D-glycero-α-L-ido-7-octenopyranoside

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Technology Process of (2-trimethylsilylethoxy)methyl 2,4,6,7,8-pentadeoxy-3-O-(4-methoxybenzyl)-2,4,6-tri-C-methyl-D-glycero-α-L-ido-7-octenopyranoside

There total 9 articles about (2-trimethylsilylethoxy)methyl 2,4,6,7,8-pentadeoxy-3-O-(4-methoxybenzyl)-2,4,6-tri-C-methyl-D-glycero-α-L-ido-7-octenopyranoside 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: 42.6%

: 76513-69-4
(2-trimethylethylsilylethoxy)methyl chloride

: 163228-71-5
(2R,3S,4R,5S,6R)-5-Hydroxy-3-(4-methoxy-benzyloxy)-2,4,6-trimethyl-oct-7-enal

: 158586-18-6
(2-trimethylsilylethoxy)methyl 2,4,6,7,8-pentadeoxy-3-O-(4-methoxybenzyl)-2,4,6-tri-C-methyl-D-glycero-α-L-ido-7-octenopyranoside

: (2-trimethylsilylethoxy)methyl 2,4,6,7,8-pentadeoxy-3-O-(4-methoxybenzyl)-2,4,6-tri-C-methyl-D-glycero-β-L-ido-7-octenopyranoside

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 25 ℃; for 20h;
DOI:10.1246/bcsj.68.967

Reference yield:

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 158586-18-6
(2-trimethylsilylethoxy)methyl 2,4,6,7,8-pentadeoxy-3-O-(4-methoxybenzyl)-2,4,6-tri-C-methyl-D-glycero-α-L-ido-7-octenopyranoside

Guidance literature:: Multi-step reaction with 9 steps

1: 83 percent / dl-10-camphorsulfonic acid / CH₂Cl₂ / 3 h / 25 °C

2: 84 percent / OsO₄, NMO, water / acetone / 20 h / 25 °C

3: NaIO₄ / H₂O; tetrahydrofuran / 1 h / 25 °C

4: 1.) t-BuOK, n-BuLi, 2.) B-(-)-methoxydiisopinocampheylborane, 3.) BF₃*OEt₂, 4.) aq. H₂O₂, aq. NaOH

5: 92 percent / imidazole / dimethylformamide / 3 h / 50 °C

6: 98 percent / DIBAL / CH₂Cl₂ / 0.5 h / 0 °C

7: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 0.5 h, 2.) CH₂Cl₂, from -78 deg C to 0 deg C, 0.5 h

8: 46percent aq. HF / acetonitrile / 0.5 h / 25 °C

9: 46.8 percent / i-Pr₂NEt / CH₂Cl₂ / 20 h / 25 °C

With 1H-imidazole; sodium hydroxide; sodium periodate; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; oxalyl dichloride; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; hydrogen fluoride; potassium tert-butylate; water; dihydrogen peroxide; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; (-)-B-methoxydiisopinocampheylborane; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.1246/bcsj.68.967

Reference yield:

: (2RS,4S,5S)-2-(4-methoxyphenyl)-5-methyl-4((R)-methylallyl)-[1,3]dioxane

: 158586-18-6
(2-trimethylsilylethoxy)methyl 2,4,6,7,8-pentadeoxy-3-O-(4-methoxybenzyl)-2,4,6-tri-C-methyl-D-glycero-α-L-ido-7-octenopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1: 84 percent / OsO₄, NMO, water / acetone / 20 h / 25 °C

2: NaIO₄ / H₂O; tetrahydrofuran / 1 h / 25 °C

3: 1.) t-BuOK, n-BuLi, 2.) B-(-)-methoxydiisopinocampheylborane, 3.) BF₃*OEt₂, 4.) aq. H₂O₂, aq. NaOH

4: 92 percent / imidazole / dimethylformamide / 3 h / 50 °C

5: 98 percent / DIBAL / CH₂Cl₂ / 0.5 h / 0 °C

6: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 0.5 h, 2.) CH₂Cl₂, from -78 deg C to 0 deg C, 0.5 h

7: 46percent aq. HF / acetonitrile / 0.5 h / 25 °C

8: 46.8 percent / i-Pr₂NEt / CH₂Cl₂ / 20 h / 25 °C

With 1H-imidazole; sodium hydroxide; sodium periodate; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; oxalyl dichloride; boron trifluoride diethyl etherate; hydrogen fluoride; potassium tert-butylate; water; dihydrogen peroxide; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; (-)-B-methoxydiisopinocampheylborane; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.1246/bcsj.68.967