(R)-3-[(2R,4S,6R,8R,10S)-10-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-8-(4-methoxy-benzyloxymethyl)-1,7-dioxa-spiro[5.5]undec-2-ylmethyl]-2-methyl-but-3-en-1-ol

Base Information

Chemical Name:(R)-3-[(2R,4S,6R,8R,10S)-10-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-8-(4-methoxy-benzyloxymethyl)-1,7-dioxa-spiro[5.5]undec-2-ylmethyl]-2-methyl-but-3-en-1-ol
CAS No.:868267-02-1
Molecular Formula:C₃₁H₅₂O₇Si
Molecular Weight:564.835
Hs Code.:

(R)-3-[(2R,4S,6R,8R,10S)-10-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-8-(4-methoxy-benzyloxymethyl)-1,7-dioxa-spiro[5.5]undec-2-ylmethyl]-2-methyl-but-3-en-1-ol

Synonyms:(R)-3-[(2R,4S,6R,8R,10S)-10-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-8-(4-methoxy-benzyloxymethyl)-1,7-dioxa-spiro[5.5]undec-2-ylmethyl]-2-methyl-but-3-en-1-ol

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Chemical Property of (R)-3-[(2R,4S,6R,8R,10S)-10-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-8-(4-methoxy-benzyloxymethyl)-1,7-dioxa-spiro[5.5]undec-2-ylmethyl]-2-methyl-but-3-en-1-ol

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Technology Process of (R)-3-[(2R,4S,6R,8R,10S)-10-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-8-(4-methoxy-benzyloxymethyl)-1,7-dioxa-spiro[5.5]undec-2-ylmethyl]-2-methyl-but-3-en-1-ol

There total 12 articles about (R)-3-[(2R,4S,6R,8R,10S)-10-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-8-(4-methoxy-benzyloxymethyl)-1,7-dioxa-spiro[5.5]undec-2-ylmethyl]-2-methyl-but-3-en-1-ol 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%

: 868267-01-0
(2R,4S,6R,8R,10S)-4-(tert-Butyl-dimethyl-silanyloxy)-8-[(R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-2-methylene-butyl]-10-methoxy-2-(4-methoxy-benzyloxymethyl)-1,7-dioxa-spiro[5.5]undecane

: 868267-02-1
(R)-3-[(2R,4S,6R,8R,10S)-10-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-8-(4-methoxy-benzyloxymethyl)-1,7-dioxa-spiro[5.5]undec-2-ylmethyl]-2-methyl-but-3-en-1-ol

Guidance literature:: With pyridine; pyridine hydrogenfluoride; In tetrahydrofuran; at 20 ℃; for 7h;
DOI:10.1002/anie.200502008

Reference yield:

: 2-(1-methyl-2-triethylsilanyloxy-ethyl)-4-triethylsilanyloxy-hept-1-en-6-yne

: 868267-02-1
(R)-3-[(2R,4S,6R,8R,10S)-10-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-8-(4-methoxy-benzyloxymethyl)-1,7-dioxa-spiro[5.5]undec-2-ylmethyl]-2-methyl-but-3-en-1-ol

Guidance literature:: Multi-step reaction with 10 steps

1: i-PrMgCl / tetrahydrofuran / 1 h / -20 °C

2: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

3: 97 percent / NaOMe / methanol; CH₂Cl₂ / 16 h / -10 - 20 °C

4: aq. HClO₄ / acetonitrile; CH₂Cl₂ / 0.5 h / 20 °C

5: PhI(Tfa)2 / 0.67 h / 0 °C

6: aq. NaHCO₃; AcOH / tetrahydrofuran / 6 h / 30 °C

7: imidazole / dimethylformamide / 14 h / 20 °C

8: 87 percent / NaBH₄; CaCl₃*7H₂O / tetrahydrofuran; methanol / 1 h / -78 °C

9: 96 percent / NaH / tetrahydrofuran / 22 h / 0 - 20 °C

10: 75 percent / HF*pyridine; pyridine / tetrahydrofuran / 7 h / 20 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; perchloric acid; CaCl₃*7H₂O; isopropylmagnesium chloride; sodium methylate; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; pyridine hydrogenfluoride; acetic acid; bis-[(trifluoroacetoxy)iodo]benzene; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 2: Dess-Martin oxidation;
DOI:10.1002/anie.200502008

Reference yield:

: 868266-87-9
1-[6-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-8-(1-methyl-2-triethylsilanyloxy-ethyl)-6-triethylsilanyloxy-non-8-en-3-yn-2-one

: 868267-02-1
(R)-3-[(2R,4S,6R,8R,10S)-10-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-8-(4-methoxy-benzyloxymethyl)-1,7-dioxa-spiro[5.5]undec-2-ylmethyl]-2-methyl-but-3-en-1-ol

Guidance literature:: Multi-step reaction with 8 steps

1: 97 percent / NaOMe / methanol; CH₂Cl₂ / 16 h / -10 - 20 °C

2: aq. HClO₄ / acetonitrile; CH₂Cl₂ / 0.5 h / 20 °C

3: PhI(Tfa)2 / 0.67 h / 0 °C

4: aq. NaHCO₃; AcOH / tetrahydrofuran / 6 h / 30 °C

5: imidazole / dimethylformamide / 14 h / 20 °C

6: 87 percent / NaBH₄; CaCl₃*7H₂O / tetrahydrofuran; methanol / 1 h / -78 °C

7: 96 percent / NaH / tetrahydrofuran / 22 h / 0 - 20 °C

8: 75 percent / HF*pyridine; pyridine / tetrahydrofuran / 7 h / 20 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; perchloric acid; CaCl₃*7H₂O; sodium methylate; sodium hydride; sodium hydrogencarbonate; pyridine hydrogenfluoride; acetic acid; bis-[(trifluoroacetoxy)iodo]benzene; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/anie.200502008