(-)-(1R,3R,5R)-3,5-dihydroxy-1-(2-hydroxymethyl)-6-{(4R,6S)-6-{(2R)-2-acetoxy-4-[(triisopropylsilyl)oxy]butyl}-2,2-dimethyl-1,3-dioxan-4-yl}-hexan-1-yl 4-methoxybenzoate

Base Information

Chemical Name:(-)-(1R,3R,5R)-3,5-dihydroxy-1-(2-hydroxymethyl)-6-{(4R,6S)-6-{(2R)-2-acetoxy-4-[(triisopropylsilyl)oxy]butyl}-2,2-dimethyl-1,3-dioxan-4-yl}-hexan-1-yl 4-methoxybenzoate
CAS No.:383191-66-0
Molecular Formula:C₃₇H₆₄O₁₁Si
Molecular Weight:712.994
Hs Code.:

(-)-(1R,3R,5R)-3,5-dihydroxy-1-(2-hydroxymethyl)-6-{(4R,6S)-6-{(2R)-2-acetoxy-4-[(triisopropylsilyl)oxy]butyl}-2,2-dimethyl-1,3-dioxan-4-yl}-hexan-1-yl 4-methoxybenzoate

Synonyms:(-)-(1R,3R,5R)-3,5-dihydroxy-1-(2-hydroxymethyl)-6-{(4R,6S)-6-{(2R)-2-acetoxy-4-[(triisopropylsilyl)oxy]butyl}-2,2-dimethyl-1,3-dioxan-4-yl}-hexan-1-yl 4-methoxybenzoate

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Chemical Property of (-)-(1R,3R,5R)-3,5-dihydroxy-1-(2-hydroxymethyl)-6-{(4R,6S)-6-{(2R)-2-acetoxy-4-[(triisopropylsilyl)oxy]butyl}-2,2-dimethyl-1,3-dioxan-4-yl}-hexan-1-yl 4-methoxybenzoate

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Technology Process of (-)-(1R,3R,5R)-3,5-dihydroxy-1-(2-hydroxymethyl)-6-{(4R,6S)-6-{(2R)-2-acetoxy-4-[(triisopropylsilyl)oxy]butyl}-2,2-dimethyl-1,3-dioxan-4-yl}-hexan-1-yl 4-methoxybenzoate

There total 5 articles about (-)-(1R,3R,5R)-3,5-dihydroxy-1-(2-hydroxymethyl)-6-{(4R,6S)-6-{(2R)-2-acetoxy-4-[(triisopropylsilyl)oxy]butyl}-2,2-dimethyl-1,3-dioxan-4-yl}-hexan-1-yl 4-methoxybenzoate 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: 44.0%

: (+)-(2S,4S)-tetrahydro-6-hydroxy-2-[3-[(4S,6S)-6-[(2R)-2-acetoxy-4-[(triisopropylsilyl)oxy]butyl]-2,2-dimethyl-1,3-dioxan-4-yl]-2-oxopropyl]-2H-pyran-4-yl 4-methoxybenzoate

: 383191-66-0
(-)-(1R,3R,5R)-3,5-dihydroxy-1-(2-hydroxymethyl)-6-{(4R,6S)-6-{(2R)-2-acetoxy-4-[(triisopropylsilyl)oxy]butyl}-2,2-dimethyl-1,3-dioxan-4-yl}-hexan-1-yl 4-methoxybenzoate

Guidance literature:: With tetramethylammonium borohydride; In acetic acid; acetonitrile; at 0 - 2 ℃; for 15h;
DOI:10.1021/jo010172u

Reference yield:

: 383191-64-8
(+)-(2S,4S,6S)-2-[3-[(4S,6S)-6-[(2R)-2-acetoxy-4-[(triisopropylsilyl)oxy]butyl]-2,2-dimethyl-1,3-dioxan-4-yl]-2-oxopropyl]tetrahydro-6-[(triisopropylsilyl)oxy]-2H-pyran-4-yl 4-methoxybenzoate

: 383191-66-0
(-)-(1R,3R,5R)-3,5-dihydroxy-1-(2-hydroxymethyl)-6-{(4R,6S)-6-{(2R)-2-acetoxy-4-[(triisopropylsilyl)oxy]butyl}-2,2-dimethyl-1,3-dioxan-4-yl}-hexan-1-yl 4-methoxybenzoate

Guidance literature:: Multi-step reaction with 2 steps

1: 85 percent / TBAF / tetrahydrofuran / 1 h / -78 - -50 °C

2: 44 percent / (Me₄N)BH₄ / acetonitrile; acetic acid / 15 h / 0 - 2 °C

With tetrabutyl ammonium fluoride; tetramethylammonium borohydride; In tetrahydrofuran; acetic acid; acetonitrile;
DOI:10.1021/jo010172u

Reference yield:

: (+)-(2S,4S)-2-[3-[(4S,6R)-6-[(2S)-2,4-dihydroxybutyl]-2,2-dimethyl-1,3-dioxan-4-yl]-2-oxopropyl]tetrahydro-6-hydroxy-2H-pyran-4-yl 4-methoxybenzoate

: 383191-66-0
(-)-(1R,3R,5R)-3,5-dihydroxy-1-(2-hydroxymethyl)-6-{(4R,6S)-6-{(2R)-2-acetoxy-4-[(triisopropylsilyl)oxy]butyl}-2,2-dimethyl-1,3-dioxan-4-yl}-hexan-1-yl 4-methoxybenzoate

Guidance literature:: Multi-step reaction with 5 steps

1: 73 percent / imidazole / dimethylformamide / 48 h / 20 °C

2: pyridine; DMAP / CH₂Cl₂ / 4 h / 20 °C

3: 94 mg / 18-crown-6 ether / benzene / 6 h / 80 °C

4: 85 percent / TBAF / tetrahydrofuran / 1 h / -78 - -50 °C

5: 44 percent / (Me₄N)BH₄ / acetonitrile; acetic acid / 15 h / 0 - 2 °C

With pyridine; 1H-imidazole; dmap; 18-crown-6 ether; tetrabutyl ammonium fluoride; tetramethylammonium borohydride; In tetrahydrofuran; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1021/jo010172u