methyl (2R,3S,4R,5S)-4-O-benzyl-5,6-O-isopropylidene-2,3,4,5,6-pentahydroxyhexanoate

Base Information

• Chemical Name: methyl (2R,3S,4R,5S)-4-O-benzyl-5,6-O-isopropylidene-2,3,4,5,6-pentahydroxyhexanoate
• CAS No.: 874896-89-6
• Molecular Formula: C₁₇H₂₄O₇
• Molecular Weight: 340.373

Synonyms:methyl (2R,3S,4R,5S)-4-O-benzyl-5,6-O-isopropylidene-2,3,4,5,6-pentahydroxyhexanoate

Chemical Property of methyl (2R,3S,4R,5S)-4-O-benzyl-5,6-O-isopropylidene-2,3,4,5,6-pentahydroxyhexanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of methyl (2R,3S,4R,5S)-4-O-benzyl-5,6-O-isopropylidene-2,3,4,5,6-pentahydroxyhexanoate

There total 7 articles about methyl (2R,3S,4R,5S)-4-O-benzyl-5,6-O-isopropylidene-2,3,4,5,6-pentahydroxyhexanoate 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:

(S)-(2-Chloro-acetoxy)-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-acetic acid ethyl ester (874897-00-4) → methyl (2R,3S,4R,5S)-4-O-benzyl-5,6-O-isopropylidene-2,3,4,5,6-pentahydroxyhexanoate (874896-89-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 90 percent / triethylamine; ethanol

2: 80 percent / silver(I) oxide; tetrabutylammonium iodide / acetonitrile / 12 h / Heating

3: 95 percent / lithium borohydride / methanol; diethyl ether / 2 h / 0 °C

4: oxalyl chloride; dimethyl sulfoxide / CH₂Cl₂ / 1 h / -78 °C

5: 80 percent / potassium hexamethyldisilazide; 18-crown-6 / tetrahydrofuran; toluene / 0.5 h / -78 °C

6: 65 percent / potassium ferricyanide(III); potassium carbonate; osmium tetroxide / hydroquinine 1,4-phthalazinediyl diether; methanesulfonamide / 2-methyl-propan-2-ol; H₂O / 36 h / 4 °C

With osmium(VIII) oxide; lithium borohydride; oxalyl dichloride; 18-crown-6 ether; ethanol; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; potassium carbonate; dimethyl sulfoxide; triethylamine; silver(l) oxide; potassium hexacyanoferrate(III); Hydroquinone 1,4-phthalazinediyl diether; methanesulfonamide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene; acetonitrile; tert-butyl alcohol; 4: Swern oxidation / 5: Horner-Emmons reaction / 6: Sharpless asymmetric dihydroxylation;

DOI:10.1021/jo0521192

Reference yield:

benzyl bromide (100-39-0) → methyl (2R,3S,4R,5S)-4-O-benzyl-5,6-O-isopropylidene-2,3,4,5,6-pentahydroxyhexanoate (874896-89-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 80 percent / silver(I) oxide; tetrabutylammonium iodide / acetonitrile / 12 h / Heating

2: 95 percent / lithium borohydride / methanol; diethyl ether / 2 h / 0 °C

3: oxalyl chloride; dimethyl sulfoxide / CH₂Cl₂ / 1 h / -78 °C

4: 80 percent / potassium hexamethyldisilazide; 18-crown-6 / tetrahydrofuran; toluene / 0.5 h / -78 °C

5: 65 percent / potassium ferricyanide(III); potassium carbonate; osmium tetroxide / hydroquinine 1,4-phthalazinediyl diether; methanesulfonamide / 2-methyl-propan-2-ol; H₂O / 36 h / 4 °C

With osmium(VIII) oxide; lithium borohydride; oxalyl dichloride; 18-crown-6 ether; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; potassium carbonate; dimethyl sulfoxide; silver(l) oxide; potassium hexacyanoferrate(III); Hydroquinone 1,4-phthalazinediyl diether; methanesulfonamide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene; acetonitrile; tert-butyl alcohol; 3: Swern oxidation / 4: Horner-Emmons reaction / 5: Sharpless asymmetric dihydroxylation;

DOI:10.1021/jo0521192

Reference yield:

(R)-2-Benzyloxy-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanol (104322-67-0) → methyl (2R,3S,4R,5S)-4-O-benzyl-5,6-O-isopropylidene-2,3,4,5,6-pentahydroxyhexanoate (874896-89-6)

Guidance literature:

Multi-step reaction with 3 steps

1: oxalyl chloride; dimethyl sulfoxide / CH₂Cl₂ / 1 h / -78 °C

2: 80 percent / potassium hexamethyldisilazide; 18-crown-6 / tetrahydrofuran; toluene / 0.5 h / -78 °C

3: 65 percent / potassium ferricyanide(III); potassium carbonate; osmium tetroxide / hydroquinine 1,4-phthalazinediyl diether; methanesulfonamide / 2-methyl-propan-2-ol; H₂O / 36 h / 4 °C

With osmium(VIII) oxide; oxalyl dichloride; 18-crown-6 ether; potassium hexamethylsilazane; potassium carbonate; dimethyl sulfoxide; potassium hexacyanoferrate(III); Hydroquinone 1,4-phthalazinediyl diether; methanesulfonamide; In tetrahydrofuran; dichloromethane; water; toluene; tert-butyl alcohol; 1: Swern oxidation / 2: Horner-Emmons reaction / 3: Sharpless asymmetric dihydroxylation;

DOI:10.1021/jo0521192

upstream raw materials:

(S)-(2-Chloro-acetoxy)-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-acetic acid ethyl ester

benzyl bromide

ethyl (2R)-2-[(1S)-3,3-dimethyl(2,4-dioxolanyl)]-2-hydroxyacetate

(R)-2-Benzyloxy-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanol

Downstream raw materials:

(2R,3R,4S,5S)-2,3:5,6-di(O-isopropylidene)-4-O-benzyl-2,3,4,5,6-pentahydroxyhexanal

methyl (2R,3R,4S,5S)-2,3:5,6-di(O-isopropylidene)-4-O-benzyl-2,3,4,5,6-pentahydroxyhexanoate

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