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

Base Information

• Chemical Name: (2R,3S,4R,5S)-2,3:5,6-di(O-isopropylidene)-4-O-benzyl-2,3,4,5,6-pentahydroxyhexanal
• CAS No.: 874896-66-9
• Molecular Formula: C₁₉H₂₆O₆
• Molecular Weight: 350.412
• Mol file: 874896-66-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about (2R,3S,4R,5S)-2,3:5,6-di(O-isopropylidene)-4-O-benzyl-2,3,4,5,6-pentahydroxyhexanal 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:

benzyl bromide (100-39-0) → (2R,3S,4R,5S)-2,3:5,6-di(O-isopropylidene)-4-O-benzyl-2,3,4,5,6-pentahydroxyhexanal (874896-66-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 85 percent / silver(I) oxide; potassium iodide / CH₂Cl₂ / 3 h / 20 °C

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

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

4: sodium hydride / benzene / 20 °C

5: 90 percent / potassium ferricyanide(III); potassium carbonate; osmium tetroxide / hydroquinine 1,4-phthalazinediyl diether; methanesulfonamide / 2-methyl-propan-2-ol; H₂O / 36 h / 4 °C

6: 96 percent / p-toluenesulfonic acid / acetone / 48 h / 20 °C

7: DIBAL / toluene / 1 h / -78 °C

With osmium(VIII) oxide; lithium borohydride; oxalyl dichloride; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; potassium iodide; silver(l) oxide; potassium hexacyanoferrate(III); Hydroquinone 1,4-phthalazinediyl diether; methanesulfonamide; In methanol; diethyl ether; dichloromethane; water; acetone; toluene; tert-butyl alcohol; benzene; 3: Swern oxidation / 4: Horner-Emmons reaction / 5: Sharpless asymmetric dihydroxylation;

DOI:10.1021/jo0521192

Reference yield:

2-O-benzyl-3,4-O-isopropylidene-L-threitol (84379-53-3) → (2R,3S,4R,5S)-2,3:5,6-di(O-isopropylidene)-4-O-benzyl-2,3,4,5,6-pentahydroxyhexanal (874896-66-9)

Guidance literature:

Multi-step reaction with 5 steps

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

2: sodium hydride / benzene / 20 °C

3: 90 percent / potassium ferricyanide(III); potassium carbonate; osmium tetroxide / hydroquinine 1,4-phthalazinediyl diether; methanesulfonamide / 2-methyl-propan-2-ol; H₂O / 36 h / 4 °C

4: 96 percent / p-toluenesulfonic acid / acetone / 48 h / 20 °C

5: DIBAL / toluene / 1 h / -78 °C

With osmium(VIII) oxide; oxalyl dichloride; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; potassium hexacyanoferrate(III); Hydroquinone 1,4-phthalazinediyl diether; methanesulfonamide; In dichloromethane; water; acetone; toluene; tert-butyl alcohol; benzene; 1: Swern oxidation / 2: Horner-Emmons reaction / 3: Sharpless asymmetric dihydroxylation;

DOI:10.1021/jo0521192

Reference yield:

2-O-benzyl-3,4-O-isopropylidene-L-threose (100906-42-1) → (2R,3S,4R,5S)-2,3:5,6-di(O-isopropylidene)-4-O-benzyl-2,3,4,5,6-pentahydroxyhexanal (874896-66-9)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium hydride / benzene / 20 °C

2: 90 percent / potassium ferricyanide(III); potassium carbonate; osmium tetroxide / hydroquinine 1,4-phthalazinediyl diether; methanesulfonamide / 2-methyl-propan-2-ol; H₂O / 36 h / 4 °C

3: 96 percent / p-toluenesulfonic acid / acetone / 48 h / 20 °C

4: DIBAL / toluene / 1 h / -78 °C

With osmium(VIII) oxide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; potassium hexacyanoferrate(III); Hydroquinone 1,4-phthalazinediyl diether; methanesulfonamide; In water; acetone; toluene; tert-butyl alcohol; benzene; 1: Horner-Emmons reaction / 2: Sharpless asymmetric dihydroxylation;

DOI:10.1021/jo0521192

upstream raw materials:

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

(4S,E)-ethyl 4-(benzyloxy)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enoate

(2R,3R,4S)-ethyl 4-(benzyloxy)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,3-dihydroxybutanoate

benzyl bromide