(1S,2R)-1-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-1-[(tert-butyldimethylsilyl)oxy]but-3-en-2-ol

Base Information

Chemical Name:(1S,2R)-1-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-1-[(tert-butyldimethylsilyl)oxy]but-3-en-2-ol
CAS No.:1289512-65-7
Molecular Formula:C₃₆H₆₂O₇Si₂
Molecular Weight:663.055
Hs Code.:

(1S,2R)-1-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-1-[(tert-butyldimethylsilyl)oxy]but-3-en-2-ol

Synonyms:(1S,2R)-1-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-1-[(tert-butyldimethylsilyl)oxy]but-3-en-2-ol

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Chemical Property of (1S,2R)-1-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-1-[(tert-butyldimethylsilyl)oxy]but-3-en-2-ol

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Technology Process of (1S,2R)-1-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-1-[(tert-butyldimethylsilyl)oxy]but-3-en-2-ol

There total 3 articles about (1S,2R)-1-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-1-[(tert-butyldimethylsilyl)oxy]but-3-en-2-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: 67.0%

: 1289512-63-5
(R)-2-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-2-[(tert-butyldimethylsilyl)oxy]acetaldehyde

: 1826-67-1
vinyl magnesium bromide

: 1289512-65-7
(1S,2R)-1-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-1-[(tert-butyldimethylsilyl)oxy]but-3-en-2-ol

: C₃₆H₆₂O₇Si₂

Guidance literature:: (R)-2-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-2-[(tert-butyldimethylsilyl)oxy]acetaldehyde; vinyl magnesium bromide; In tetrahydrofuran; at -78 ℃; for 0.416667h; Inert atmosphere;

With ammonium chloride; In tetrahydrofuran; water; at -78 - 20 ℃; optical yield given as %de; Inert atmosphere;
DOI:10.1002/ejoc.201001411

Reference yield:

: 1063713-63-2
(1S,3R,5S)-1-benzyloxymethyl-3-[(2R,3R,5R)-5-[(S)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-furan-2-yl]-5-methyl-2,8-dioxa-bicyclo[3.2.1]octane

: 1289512-65-7
(1S,2R)-1-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-1-[(tert-butyldimethylsilyl)oxy]but-3-en-2-ol

: C₃₆H₆₂O₇Si₂

Guidance literature:: Multi-step reaction with 3 steps

1.1: pyridine hydrogenfluoride / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.13 h / -50 - -30 °C / Inert atmosphere

2.2: 0.75 h / -30 °C / Inert atmosphere

2.3: 0.17 h / -30 °C / Inert atmosphere

3.1: tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere

3.2: -78 - 20 °C / Inert atmosphere

With oxalyl dichloride; pyridine hydrogenfluoride; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; 2.1: Swern oxidation / 2.2: Swern oxidation / 2.3: Swern oxidation;
DOI:10.1002/ejoc.201001411

Reference yield:

: 1289512-61-3
(S)-2-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-2-[(tert-butyldimethylsilyl)oxy]ethanol

: 1289512-65-7
(1S,2R)-1-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-1-[(tert-butyldimethylsilyl)oxy]but-3-en-2-ol

: C₃₆H₆₂O₇Si₂

Guidance literature:: Multi-step reaction with 2 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.13 h / -50 - -30 °C / Inert atmosphere

1.2: 0.75 h / -30 °C / Inert atmosphere

1.3: 0.17 h / -30 °C / Inert atmosphere

2.1: tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

With oxalyl dichloride; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; 1.1: Swern oxidation / 1.2: Swern oxidation / 1.3: Swern oxidation;
DOI:10.1002/ejoc.201001411