[(2S,4S)-6-[(3S,4R,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-hept-1-ynyl]-6-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-methanol

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Chemical Name:[(2S,4S)-6-[(3S,4R,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-hept-1-ynyl]-6-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-methanol
CAS No.:119662-87-2
Molecular Formula:C₃₀H₅₀O₆Si
Molecular Weight:534.809
Hs Code.:

Synonyms:[(2S,4S)-6-[(3S,4R,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-hept-1-ynyl]-6-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-methanol

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Chemical Property of [(2S,4S)-6-[(3S,4R,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-hept-1-ynyl]-6-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-methanol

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Technology Process of [(2S,4S)-6-[(3S,4R,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-hept-1-ynyl]-6-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-methanol

There total 19 articles about [(2S,4S)-6-[(3S,4R,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-hept-1-ynyl]-6-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-methanol 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: 88.0%

: 67-56-1
methanol

: 119649-99-9
(2S,7S,8R,9S)-8-(tert-Butyl-dimethyl-silanyloxy)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-(4-methoxy-benzyloxy)-7,9-dimethyl-undec-5-yn-4-one

: 119662-87-2
[(2S,4S)-6-[(3S,4R,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-hept-1-ynyl]-6-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-methanol

Guidance literature:: With camphor-10-sulfonic acid; for 3h; Ambient temperature;
DOI:10.1021/ja00112a006

Reference yield: 84.0%

: 119649-99-9
(2S,7S,8R,9S)-8-(tert-Butyl-dimethyl-silanyloxy)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-(4-methoxy-benzyloxy)-7,9-dimethyl-undec-5-yn-4-one

: 119662-87-2
[(2S,4S)-6-[(3S,4R,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-hept-1-ynyl]-6-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-methanol

Guidance literature:: camphor-10-sulfonic acid; In methanol; for 1h;
DOI:10.1016/0040-4039(88)85048-2

Reference yield:

: 1730-97-8
(S)-2-methylbutyraldehyde

: 119662-87-2
[(2S,4S)-6-[(3S,4R,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-hept-1-ynyl]-6-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-methanol

Guidance literature:: Multi-step reaction with 8 steps

1: 53 percent / CrCl₃, LiAlH₄ / tetrahydrofuran / 3 h / Ambient temperature

2: 86 percent / CH₂Cl₂ / 3 h

3: 1.) O₃, 2.) Me₂S / 1.) CH₃OH, -78 deg C, 10 min, 2.) CH₃OH, RT, 12 h

4: 1.) Zn, 2.) Ph₃P / 1.) CH₂Cl₂, 30 min, 2.) CH₂Cl₂, 4 h

5: 86 percent / n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 - 20 °C

6: 1.) EtMgBr / 1.) THF, ether, from 0 deg C to RT, 2.) THF, ether, -78 deg C, 15 min

7: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 0.5 h, 2.) CH₂Cl₂, from -78 deg C to RT

8: 88 percent / camphorsulfonic acid / 3 h / Ambient temperature

With chromium chloride; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; dimethylsulfide; camphor-10-sulfonic acid; ethylmagnesium bromide; ozone; dimethyl sulfoxide; triethylamine; triphenylphosphine; zinc; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ja00112a006