(Z)-2-[(2S,3S,4S,5R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yloxymethyl]-3-[(1S,2R,6R)-6-isopropyl-3-methyl-2-((2S,3S)-3-methyl-2,3-bis-triethylsilanyloxy-pent-4-ynyl)-cyclohex-3-enyl]-propenal

Base Information

Chemical Name:(Z)-2-[(2S,3S,4S,5R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yloxymethyl]-3-[(1S,2R,6R)-6-isopropyl-3-methyl-2-((2S,3S)-3-methyl-2,3-bis-triethylsilanyloxy-pent-4-ynyl)-cyclohex-3-enyl]-propenal
CAS No.:201142-54-3
Molecular Formula:C₅₇H₁₀₂O₉Si₄
Molecular Weight:1043.77
Hs Code.:

(Z)-2-[(2S,3S,4S,5R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yloxymethyl]-3-[(1S,2R,6R)-6-isopropyl-3-methyl-2-((2S,3S)-3-methyl-2,3-bis-triethylsilanyloxy-pent-4-ynyl)-cyclohex-3-enyl]-propenal

Synonyms:(Z)-2-[(2S,3S,4S,5R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yloxymethyl]-3-[(1S,2R,6R)-6-isopropyl-3-methyl-2-((2S,3S)-3-methyl-2,3-bis-triethylsilanyloxy-pent-4-ynyl)-cyclohex-3-enyl]-propenal

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Chemical Property of (Z)-2-[(2S,3S,4S,5R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yloxymethyl]-3-[(1S,2R,6R)-6-isopropyl-3-methyl-2-((2S,3S)-3-methyl-2,3-bis-triethylsilanyloxy-pent-4-ynyl)-cyclohex-3-enyl]-propenal

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Technology Process of (Z)-2-[(2S,3S,4S,5R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yloxymethyl]-3-[(1S,2R,6R)-6-isopropyl-3-methyl-2-((2S,3S)-3-methyl-2,3-bis-triethylsilanyloxy-pent-4-ynyl)-cyclohex-3-enyl]-propenal

There total 16 articles about (Z)-2-[(2S,3S,4S,5R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yloxymethyl]-3-[(1S,2R,6R)-6-isopropyl-3-methyl-2-((2S,3S)-3-methyl-2,3-bis-triethylsilanyloxy-pent-4-ynyl)-cyclohex-3-enyl]-propenal 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: 75.0%

: 201142-44-1
(Z)-2-Hydroxymethyl-3-[(1S,2R,6R)-6-isopropyl-3-methyl-2-((2S,3S)-3-methyl-2,3-bis-triethylsilanyloxy-pent-4-ynyl)-cyclohex-3-enyl]-propenal

: 201142-52-1
2,2,2-Trichloro-acetimidic acid (2S,3S,4S,5R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl ester

: 201142-53-2
(Z)-2-[(2R,3S,4S,5R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yloxymethyl]-3-[(1S,2R,6R)-6-isopropyl-3-methyl-2-((2S,3S)-3-methyl-2,3-bis-triethylsilanyloxy-pent-4-ynyl)-cyclohex-3-enyl]-propenal

: 201142-54-3
(Z)-2-[(2S,3S,4S,5R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yloxymethyl]-3-[(1S,2R,6R)-6-isopropyl-3-methyl-2-((2S,3S)-3-methyl-2,3-bis-triethylsilanyloxy-pent-4-ynyl)-cyclohex-3-enyl]-propenal

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In 1,4-dioxane; toluene; at 0 ℃; for 0.166667h; Yields of byproduct given;
DOI:10.1021/ja9810639

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 201142-54-3
(Z)-2-[(2S,3S,4S,5R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yloxymethyl]-3-[(1S,2R,6R)-6-isopropyl-3-methyl-2-((2S,3S)-3-methyl-2,3-bis-triethylsilanyloxy-pent-4-ynyl)-cyclohex-3-enyl]-propenal

Guidance literature:: Multi-step reaction with 4 steps

1: 97 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

2: 80 percent / NBS, pyridine / acetone; H₂O

3: 93 percent / NaH / CH₂Cl₂ / 3.5 h / 25 °C

4: TMSOTf / hexane / -78 °C

With pyridine; N-Bromosuccinimide; trimethylsilyl trifluoromethanesulfonate; sodium hydride; triethylamine; In hexane; dichloromethane; water; acetone;
DOI:10.1021/ja9810639

Reference yield:

: 824-94-2
p-methoxybenzyl chloride

: 201142-54-3
(Z)-2-[(2S,3S,4S,5R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yloxymethyl]-3-[(1S,2R,6R)-6-isopropyl-3-methyl-2-((2S,3S)-3-methyl-2,3-bis-triethylsilanyloxy-pent-4-ynyl)-cyclohex-3-enyl]-propenal

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) NaH / 1.) DMF, 0 deg C, 30 min, 2.) DMF, 2 h

2: 84 percent / TsOH*H₂O, ethanediol / methanol / 6 h / 25 °C

3: 97 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

4: 80 percent / NBS, pyridine / acetone; H₂O

5: 93 percent / NaH / CH₂Cl₂ / 3.5 h / 25 °C

6: TMSOTf / hexane / -78 °C

With pyridine; N-Bromosuccinimide; trimethylsilyl trifluoromethanesulfonate; sodium hydride; toluene-4-sulfonic acid; ethylene glycol; triethylamine; In methanol; hexane; dichloromethane; water; acetone;
DOI:10.1021/ja9810639