5,7-O--1,6,8,9-tetradeoxy-4-O-<2,6-dideoxy-3-O-methyl-4-O-(triethylsilyl)-β-D-ribo-hexopyranosyl>-3-O-<(4-methoxyphenyl)methyl>-6,8-dimethyl-D-glycero-L-ido-non-8-en-2-ulose

Base Information

Chemical Name:5,7-O--1,6,8,9-tetradeoxy-4-O-<2,6-dideoxy-3-O-methyl-4-O-(triethylsilyl)-β-D-ribo-hexopyranosyl>-3-O-<(4-methoxyphenyl)methyl>-6,8-dimethyl-D-glycero-L-ido-non-8-en-2-ulose
CAS No.:129986-36-3
Molecular Formula:C₄₀H₇₀O₉Si₂
Molecular Weight:751.161
Hs Code.:

5,7-O-<bis(1,1-dimethylethyl)silylene>-1,6,8,9-tetradeoxy-4-O-<2,6-dideoxy-3-O-methyl-4-O-(triethylsilyl)-β-D-ribo-hexopyranosyl>-3-O-<(4-methoxyphenyl)methyl>-6,8-dimethyl-D-glycero-L-ido-non-8-en-2-ulose

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Chemical Property of 5,7-O--1,6,8,9-tetradeoxy-4-O-<2,6-dideoxy-3-O-methyl-4-O-(triethylsilyl)-β-D-ribo-hexopyranosyl>-3-O-<(4-methoxyphenyl)methyl>-6,8-dimethyl-D-glycero-L-ido-non-8-en-2-ulose

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Technology Process of 5,7-O--1,6,8,9-tetradeoxy-4-O-<2,6-dideoxy-3-O-methyl-4-O-(triethylsilyl)-β-D-ribo-hexopyranosyl>-3-O-<(4-methoxyphenyl)methyl>-6,8-dimethyl-D-glycero-L-ido-non-8-en-2-ulose

There total 17 articles about 5,7-O--1,6,8,9-tetradeoxy-4-O-<2,6-dideoxy-3-O-methyl-4-O-(triethylsilyl)-β-D-ribo-hexopyranosyl>-3-O-<(4-methoxyphenyl)methyl>-6,8-dimethyl-D-glycero-L-ido-non-8-en-2-ulose 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%

: 917-54-4
methyllithium

: 129986-34-1,129986-35-2,129986-48-7,129986-49-8
4,6-O--5,7,8-trideoxy-3-O-<2,6-dideoxy-3-O-methyl-4-O-(triethylsilyl)-β-D-ribo-hexopyranosyl>-N-methoxy-2-O-<(4-methoxyphenyl)methyl>-N,5,7-trimethyl-D-glycero-L-ido-oct-7-enonamide

: 129986-36-3,129986-50-1
5,7-O--1,6,8,9-tetradeoxy-4-O-<2,6-dideoxy-3-O-methyl-4-O-(triethylsilyl)-β-D-ribo-hexopyranosyl>-3-O-<(4-methoxyphenyl)methyl>-6,8-dimethyl-D-glycero-L-ido-non-8-en-2-ulose

Guidance literature:: With lithium bromide; In tetrahydrofuran; at -78 ℃; for 0.666667h;
DOI:10.1021/ja00175a038

Reference yield:

: 88920-24-5
p-methoxybenzyloxy acetic acid

: 129986-36-3,129986-50-1
5,7-O--1,6,8,9-tetradeoxy-4-O-<2,6-dideoxy-3-O-methyl-4-O-(triethylsilyl)-β-D-ribo-hexopyranosyl>-3-O-<(4-methoxyphenyl)methyl>-6,8-dimethyl-D-glycero-L-ido-non-8-en-2-ulose

Guidance literature:: Multi-step reaction with 7 steps

1: Et₃N / diethyl ether / 1.58 h / -78 - 0 °C

2: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 10 min, 2.) a) ether, -70 deg C, 45 min, b) 0 deg C, 6 h

4: 1.) Me₃Al / 1.) THF, toluene, RT, 15 min, 2.) 0 deg C, 2.25 h

5: Dess-Martin periodinane, pyridine / CH₂Cl₂ / 0.83 h / Ambient temperature

6: 70 percent / trityl perchlorate / toluene / 1.42 h / -8 - -5 °C

7: 95 percent / LiBr / tetrahydrofuran / 0.67 h / -78 °C

With pyridine; n-butyllithium; trimethylaluminum; triphenylmethyl perchlorate; Dess-Martin periodane; triethylamine; lithium bromide; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;
DOI:10.1021/ja00175a038

Reference yield:

: 129986-21-6
<2R,3S,4S>-2,4-O--3-methyl-5-methylene-1,2,4-hexanetriol

: 129986-36-3,129986-50-1
5,7-O--1,6,8,9-tetradeoxy-4-O-<2,6-dideoxy-3-O-methyl-4-O-(triethylsilyl)-β-D-ribo-hexopyranosyl>-3-O-<(4-methoxyphenyl)methyl>-6,8-dimethyl-D-glycero-L-ido-non-8-en-2-ulose

Guidance literature:: Multi-step reaction with 6 steps

1: 97 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 0.25 h / -78 °C

3: 1.) Me₃Al / 1.) THF, toluene, RT, 15 min, 2.) 0 deg C, 2.25 h

4: Dess-Martin periodinane, pyridine / CH₂Cl₂ / 0.83 h / Ambient temperature

5: 70 percent / trityl perchlorate / toluene / 1.42 h / -8 - -5 °C

6: 95 percent / LiBr / tetrahydrofuran / 0.67 h / -78 °C

With pyridine; oxalyl dichloride; trimethylaluminum; triphenylmethyl perchlorate; Dess-Martin periodane; dimethyl sulfoxide; lithium bromide; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/ja00175a038