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Cas Database

5987-33-7

5987-33-7

Identification

Synonyms:1,5-Anhydro-4,6-O-benzylidene-2-deoxy-D-ribo-hex-1-enopyranose;1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-ribo-hex-1-enitol;4,6-O-benzylidene-1,2-dideoxy-D-ribo-hex-1-enopyranose;4,6-O-Benzyliden-1.2-dideoxy-D-ribo-hex-1-enopyranose;

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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Relevant articles and documentsAll total 9 Articles be found

Stereoelectronic factors in the stereoselective epoxidation of glycals and 4-deoxypentenosides

Alberch, Laura,Cheng, Gang,Seo, Seung-Kee,Li, Xuehua,Boulineau, Fabien P.,Wei, Alexander

, p. 2532 - 2547 (2011/06/19)

Glycals and 4-deoxypentenosides (4-DPs), unsaturated pyranosides with similar structures and reactivity profiles, can exhibit a high degree of stereoselectivity upon epoxidation with dimethyldioxirane (DMDO). In most cases, the glycals and their corresponding 4-DP isosteres share the same facioselectivity, implying that the pyran substituents are largely responsible for the stereodirecting effect. Fully substituted dihydropyrans are subject to a "majority rule", in which the epoxidation is directed toward the face opposite to two of the three groups. Removing one of the substituents has a variable effect on the epoxidation outcome, depending on its position and also on the relative stereochemistry of the remaining two groups. Overall, we observe that the greatest loss in facioselectivity for glycals and 4-DPs is caused by removal of the C3 oxygen, followed by the C5/anomeric substituent, and least of all by the C4/C2 oxygen. DFT calculations based on polarized-π frontier molecular orbital (PPFMO) theory support a stereoelectronic role for the oxygen substituents in 4-DP facioselectivity, but less clearly so in the case of glycals. We conclude that the anomeric oxygen in 4-DPs contributes toward a stereoelectronic bias in facioselectivity whereas the C5 alkoxymethyl in glycals imparts a steric bias, which at times can compete with the stereodirecting effects from the other oxygen substituents.

Selective generation of free radicals from epoxides using a transition-metal radical. A powerful new tool for organic synthesis

RajanBabu,Nugent, William A.

, p. 986 - 997 (2007/10/02)

Bis(cyclopentadienyl)titanium(III) chloride reacts with epoxides by initial C-O homolysis. The regiochemistry of the opening is determined by the relative stabilities of the radicals. Depending on the reaction partners, these radicals undergo intramolecular (hex-5-enyl cyclization) or intermolecular additions to olefins. The resultant radicals are efficiently scavenged by a second equivalent of Ti(III) to afford the corresponding Ti(IV) derivative. Treatment of this intermediate with electrophiles such as H+ or halogens provides a route to functionalized cyclopentanes and other useful products. The radical initially formed from an epoxide can also be trapped by H-atom donors such as 1,4-cyclohexadiene or tert-butyl thiol, resulting in an overall reduction of the epoxide. In the absence of a H-atom donor or an olefin, this radical is trapped by Ti(III), resulting in a β-oxido-Ti organometallic species which undergoes facile elimination to give an olefin. The reaction conditions are remarkably mild and are applicable to very sensitive substrates.

Free radical mediated reduction and deoxygenation of epoxides

Rajanbabu,Nugent, William A.,Beattie, Margaret S.

, p. 6408 - 6409 (2007/10/02)

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Highly Selective Metal-Graphite-Induced Reductions of Deoxy Halo Sugars

Fuerstner, Alois,Weidmann, Hans

, p. 2307 - 2311 (2007/10/02)

To explore the applicability of highly active metal-graphite reducing agents to polyfunctional compounds a variety of suitably protected chloro-, bromodeoxy-, and deoxyiodohexopyranosides and hexofuranoses were each treated with potassium-graphite laminat

REACTION OF BUTYLLITHIUM WITH BENZYLIDENE ACETALS OF ALDOPYRANOSIDES AND 1,5-ANHYDROALDITOLS

Horton, Derek,Weckerle, Wolfgang

, p. 305 - 312 (2007/10/02)

Under suitable conditions, butyllithium selectively cleaves 5-membered benzylidene acetals (1,3-dioxolane ring) leaving the 6-membered analogs (1,3-dioxane ring) intact in aldopyranoside and 1,5-anhydroalditol derivatives.The usual course of the reaction

Process route upstream and downstream products

Process route

Trimethyl-[2-((4aR,8S,8aS)-2-phenyl-4,4a,8,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-yloxymethoxy)-ethyl]-silane
76513-66-1

Trimethyl-[2-((4aR,8S,8aS)-2-phenyl-4,4a,8,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-yloxymethoxy)-ethyl]-silane

4,6-O-benzylidene-D-allal
5987-33-7,167074-37-5

4,6-O-benzylidene-D-allal

ethene
74-85-1

ethene

trimethylsilyl fluoride
420-56-4

trimethylsilyl fluoride

Conditions
Conditions Yield
With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 45 ℃; for 11h;
86%
Methyl-4,6-O-benzyliden-2-deoxy-2-jod-α-D-altropyranosid
14125-73-6

Methyl-4,6-O-benzyliden-2-deoxy-2-jod-α-D-altropyranosid

4,6-O-benzylidene-D-allal
5987-33-7,167074-37-5

4,6-O-benzylidene-D-allal

Conditions
Conditions Yield
With silver-graphite; zinc; In tetrahydrofuran; at 20 ℃; for 0.666667h;
90%
methyl 2,3-anhydro-4,6-benzylidene-α-D-allopyranoside
66537-92-6

methyl 2,3-anhydro-4,6-benzylidene-α-D-allopyranoside

4,6-O-benzylidene-D-allal
5987-33-7,167074-37-5

4,6-O-benzylidene-D-allal

methyl 4,6-O-benzylidene-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
3169-98-0

methyl 4,6-O-benzylidene-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

Conditions
Conditions Yield
With bis(cyclopentadienyl)titanium (III) chloride; In tetrahydrofuran;
78%
16%
methyl 2,3-anhydro-4,6-benzylidene-α-D-allopyranoside
66537-92-6

methyl 2,3-anhydro-4,6-benzylidene-α-D-allopyranoside

4,6-O-benzylidene-D-allal
5987-33-7,167074-37-5

4,6-O-benzylidene-D-allal

methyl 4,6-O-benzylidene-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
3169-98-0

methyl 4,6-O-benzylidene-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

methyl 4,6-O-benzylidene-3-deoxy-α-D-glucopyranoside
65530-28-1

methyl 4,6-O-benzylidene-3-deoxy-α-D-glucopyranoside

Conditions
Conditions Yield
With bis(cyclopentadienyl)titanium (III) chloride; In tetrahydrofuran;
65%
12%
Conditions
Conditions Yield
With bis(cyclopentadienyl)titanium (III) chloride;
78%
16%
1,5-anhydro-2,3:4,6-di-O-benzylidene-D-allitol
63598-37-8

1,5-anhydro-2,3:4,6-di-O-benzylidene-D-allitol

4,6-O-benzylidene-D-allal
5987-33-7,167074-37-5

4,6-O-benzylidene-D-allal

1,5-anhydro-4,6-O-benzylidene-3-deoxy-D-erythro-hex-2-ulose
116558-22-6

1,5-anhydro-4,6-O-benzylidene-3-deoxy-D-erythro-hex-2-ulose

Conditions
Conditions Yield
With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 1.5h;
51%
3%
methyl 2,3-anhydro-4,6-O-benzylidene-α-D-allopyranoside
3150-15-0

methyl 2,3-anhydro-4,6-O-benzylidene-α-D-allopyranoside

n-decyllithium
4416-59-5

n-decyllithium

4,6-O-benzylidene-D-allal
5987-33-7,167074-37-5

4,6-O-benzylidene-D-allal

methyl 4,6-O-benzylidene-2-C-decyl-2-deoxy-α-D-allopyranoside

methyl 4,6-O-benzylidene-2-C-decyl-2-deoxy-α-D-allopyranoside

Conditions
Conditions Yield
With copper(l) cyanide; In tetrahydrofuran; diethyl ether; at -5 - 0 ℃; for 1h;
46%
52%
methyl 2,3-anhydro-4,6-O-benzylidene-α-D-allopyranoside
3150-15-0

methyl 2,3-anhydro-4,6-O-benzylidene-α-D-allopyranoside

ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

4,6-O-benzylidene-D-allal
5987-33-7,167074-37-5

4,6-O-benzylidene-D-allal

methyl 4,6-O-benzylidene-2-deoxy-α-D-altropyranoside
16718-95-9

methyl 4,6-O-benzylidene-2-deoxy-α-D-altropyranoside

methyl 4,6-O-benzylidene-2-bromo-2-deoxy-α-D-altropyranoside
19465-09-9

methyl 4,6-O-benzylidene-2-bromo-2-deoxy-α-D-altropyranoside

Conditions
Conditions Yield
With triisobutylaluminum; In tetrahydrofuran; at -78 - 20 ℃; for 20h;
23%
11%
59%
methyl 2,3-anhydro-4,6-O-benzylidene-α-D-allopyranoside
3150-15-0

methyl 2,3-anhydro-4,6-O-benzylidene-α-D-allopyranoside

ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

4,6-O-benzylidene-D-allal
5987-33-7,167074-37-5

4,6-O-benzylidene-D-allal

methyl 4,6-O-benzylidene-2-deoxy-2-C-ethyl-α-D-altropyranoside
85982-82-7

methyl 4,6-O-benzylidene-2-deoxy-2-C-ethyl-α-D-altropyranoside

methyl 4,6-O-benzylidene-3-deoxy-3-C-ethyl-α-D-altropyranoside
85982-81-6

methyl 4,6-O-benzylidene-3-deoxy-3-C-ethyl-α-D-altropyranoside

Conditions
Conditions Yield
With copper(l) iodide; lithium dimethylcuprate; In tetrahydrofuran; at -78 - 20 ℃; for 5h;
22%
7%
70%
C<sub>19</sub>H<sub>18</sub>O<sub>4</sub>S

C19H18O4S

4,6-O-benzylidene-D-allal
5987-33-7,167074-37-5

4,6-O-benzylidene-D-allal

Conditions
Conditions Yield
With diethylamine; In tetrahydrofuran; at 20 ℃;

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  • Antimex Chemical Limied
  • Business Type:Lab/Research institutions
  • Contact Tel:0086-21-50563169
  • Emails:anthony@antimex.com
  • Main Products:163
  • Country:China (Mainland)
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