[(4R,5R,6R)-5-Benzyloxy-6-((Z)-(S)-1-methoxy-2,2-dimethyl-pent-3-enyl)-[1,3]dioxan-4-ylmethoxy]-tert-butyl-diphenyl-silane

Base Information

Chemical Name:[(4R,5R,6R)-5-Benzyloxy-6-((Z)-(S)-1-methoxy-2,2-dimethyl-pent-3-enyl)-[1,3]dioxan-4-ylmethoxy]-tert-butyl-diphenyl-silane
CAS No.:289667-11-4
Molecular Formula:C₃₆H₄₈O₅Si
Molecular Weight:588.86
Hs Code.:

Synonyms:[(4R,5R,6R)-5-Benzyloxy-6-((Z)-(S)-1-methoxy-2,2-dimethyl-pent-3-enyl)-[1,3]dioxan-4-ylmethoxy]-tert-butyl-diphenyl-silane

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Chemical Property of [(4R,5R,6R)-5-Benzyloxy-6-((Z)-(S)-1-methoxy-2,2-dimethyl-pent-3-enyl)-[1,3]dioxan-4-ylmethoxy]-tert-butyl-diphenyl-silane

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Technology Process of [(4R,5R,6R)-5-Benzyloxy-6-((Z)-(S)-1-methoxy-2,2-dimethyl-pent-3-enyl)-[1,3]dioxan-4-ylmethoxy]-tert-butyl-diphenyl-silane

There total 12 articles about [(4R,5R,6R)-5-Benzyloxy-6-((Z)-(S)-1-methoxy-2,2-dimethyl-pent-3-enyl)-[1,3]dioxan-4-ylmethoxy]-tert-butyl-diphenyl-silane 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: 100.0%

: 1530-32-1
ethyltriphenylphosphonium bromide

: 289666-94-0
(+)-(3S,4R,5R,6R)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-methoxy-4,6-methylenedioxyheptanal

: 289667-11-4
[(4R,5R,6R)-5-Benzyloxy-6-((Z)-(S)-1-methoxy-2,2-dimethyl-pent-3-enyl)-[1,3]dioxan-4-ylmethoxy]-tert-butyl-diphenyl-silane

Guidance literature:: With n-butyllithium; at 0 ℃;
DOI:10.1021/ol000072v

Reference yield:

: 108341-87-3
(2R,3R)-3-O-benzyl-1,2-O-isopropylidene-4-pentene-1,2,3-triol

: 289667-11-4
[(4R,5R,6R)-5-Benzyloxy-6-((Z)-(S)-1-methoxy-2,2-dimethyl-pent-3-enyl)-[1,3]dioxan-4-ylmethoxy]-tert-butyl-diphenyl-silane

Guidance literature:: Multi-step reaction with 12 steps

1: OsO₄; NMO

2: DMAP; Et₃N

3: 98 percent / AcOH; H₂O / tetrahydrofuran / 55 °C

4: 89 percent / pyridine

5: 88 percent / P₂O₅

6: 99 percent / DIBALH / 0 °C

7: (COCl)2; DMSO; Et₃N / -78 - -40 °C

8: TiCl₄ / CH₂Cl₂ / -78 °C

9: 95 percent / NaH / 0 - 20 °C

10: 100 percent / DIBALH / 0 °C

11: 97 percent / SO₃*Py; DMSO; Et₃N

12: 100 percent / BuLi / 0 °C

With pyridine; dmap; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; oxalyl dichloride; pyridine-SO₃ complex; water; phosphorus pentoxide; titanium tetrachloride; sodium hydride; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 1: hydroxylation / 2: silylation / 3: Hydrolysis / 4: Esterification / 5: cyclocondensation / 6: Reduction / 7: Swern oxidation / 8: Condensation / 9: Methylation / 10: Reduction / 11: Oxidation / 12: Wittig reaction;
DOI:10.1021/ol000072v

Reference yield:

: (2RS,3R,4R)-3-benzyloxy-4,5-isopropylidenedioxy-1,2-pentanediol

: 289667-11-4
[(4R,5R,6R)-5-Benzyloxy-6-((Z)-(S)-1-methoxy-2,2-dimethyl-pent-3-enyl)-[1,3]dioxan-4-ylmethoxy]-tert-butyl-diphenyl-silane

Guidance literature:: Multi-step reaction with 11 steps

1: DMAP; Et₃N

2: 98 percent / AcOH; H₂O / tetrahydrofuran / 55 °C

3: 89 percent / pyridine

4: 88 percent / P₂O₅

5: 99 percent / DIBALH / 0 °C

6: (COCl)2; DMSO; Et₃N / -78 - -40 °C

7: TiCl₄ / CH₂Cl₂ / -78 °C

8: 95 percent / NaH / 0 - 20 °C

9: 100 percent / DIBALH / 0 °C

10: 97 percent / SO₃*Py; DMSO; Et₃N

11: 100 percent / BuLi / 0 °C

With pyridine; dmap; n-butyllithium; oxalyl dichloride; pyridine-SO₃ complex; water; phosphorus pentoxide; titanium tetrachloride; sodium hydride; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 1: silylation / 2: Hydrolysis / 3: Esterification / 4: cyclocondensation / 5: Reduction / 6: Swern oxidation / 7: Condensation / 8: Methylation / 9: Reduction / 10: Oxidation / 11: Wittig reaction;
DOI:10.1021/ol000072v