(2R,3S)-3-O-benzyl-1,2-O-isopropylidenepentane-1,2,3,5-tetrol

Base Information

• Chemical Name: (2R,3S)-3-O-benzyl-1,2-O-isopropylidenepentane-1,2,3,5-tetrol
• CAS No.: 93170-28-6
• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.337
• Mol file: 93170-28-6.mol

Synonyms:(2R,3S)-3-O-benzyl-1,2-O-isopropylidenepentane-1,2,3,5-tetrol

Chemical Property of (2R,3S)-3-O-benzyl-1,2-O-isopropylidenepentane-1,2,3,5-tetrol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-3-O-benzyl-1,2-O-isopropylidenepentane-1,2,3,5-tetrol

There total 14 articles about (2R,3S)-3-O-benzyl-1,2-O-isopropylidenepentane-1,2,3,5-tetrol 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)-3-O-benzyl-1,2-O-isopropylidenepentane-1,2,3,5-tetrol (93170-28-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) NaH / 1.) THHF, DMF, rt., 0.5 h, 2.) THF, DMF, 12 h

2: 82 percent / pyridine, Br₂ / acetone; H₂O / -20 deg C, then room t., 2 h; with var. reagents

3: 196.0 mg / DIBAL / CH₂Cl₂; hexane / 0.75 h / -78 °C

4: Et₃N / DMAP / CH₂Cl₂ / 5 h / Ambient temperature

5: 1., OsO₄, 2.) NaIO₄ / 1.) dioxan-water, room t., 15 min, 2., dioxan-water, 4 h

6: LiAlH₄ / diethyl ether / 0 deg C, to room t.,

7: NaIO₄ / methanol; H₂O / 1 h / Ambient temperature

8: NaBH₄ / methanol / 0 deg C, then 12 h, room t.,

With pyridine; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; bromine; sodium hydride; diisobutylaluminium hydride; triethylamine; dmap; In methanol; diethyl ether; hexane; dichloromethane; water; acetone;

DOI:10.1016/S0040-4020(01)86159-7

Reference yield:

(2R,3S)-3-O-benzyl-1,2-O-isopropylidene-4-<2-(5-methylfuryl)>-1,2,3-butanetriol (93170-24-2) → (2R,3S)-3-O-benzyl-1,2-O-isopropylidenepentane-1,2,3,5-tetrol (93170-28-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 82 percent / pyridine, Br₂ / acetone; H₂O / -20 deg C, then room t., 2 h; with var. reagents

2: 196.0 mg / DIBAL / CH₂Cl₂; hexane / 0.75 h / -78 °C

3: Et₃N / DMAP / CH₂Cl₂ / 5 h / Ambient temperature

4: 1., OsO₄, 2.) NaIO₄ / 1.) dioxan-water, room t., 15 min, 2., dioxan-water, 4 h

5: LiAlH₄ / diethyl ether / 0 deg C, to room t.,

6: NaIO₄ / methanol; H₂O / 1 h / Ambient temperature

7: NaBH₄ / methanol / 0 deg C, then 12 h, room t.,

With pyridine; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; bromine; diisobutylaluminium hydride; triethylamine; dmap; In methanol; diethyl ether; hexane; dichloromethane; water; acetone;

DOI:10.1016/S0040-4020(01)86159-7

Reference yield:

2,3-isopropylidene-glyceraldehyde (15186-48-8) → (2R,3S)-3-O-benzyl-1,2-O-isopropylidenepentane-1,2,3,5-tetrol (93170-28-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 22 percent / CH₂Cl₂ / 24 h / 50 °C / 15001200 Torr

2: 1.) NaH / 1.) THHF, DMF, rt., 0.5 h, 2.) THF, DMF, 12 h

3: 82 percent / pyridine, Br₂ / acetone; H₂O / -20 deg C, then room t., 2 h; with var. reagents

4: 196.0 mg / DIBAL / CH₂Cl₂; hexane / 0.75 h / -78 °C

5: Et₃N / DMAP / CH₂Cl₂ / 5 h / Ambient temperature

6: 1., OsO₄, 2.) NaIO₄ / 1.) dioxan-water, room t., 15 min, 2., dioxan-water, 4 h

7: LiAlH₄ / diethyl ether / 0 deg C, to room t.,

8: NaIO₄ / methanol; H₂O / 1 h / Ambient temperature

9: NaBH₄ / methanol / 0 deg C, then 12 h, room t.,

With pyridine; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; bromine; sodium hydride; diisobutylaluminium hydride; triethylamine; dmap; In methanol; diethyl ether; hexane; dichloromethane; water; acetone;

DOI:10.1016/S0040-4020(01)86159-7

upstream raw materials:

(3S,4R)-3-O-benzyl-4,5-O-isopropylidene-3,4,5-trihydroxypentanal

(R)-4-((S)-1-(benzyloxy)but-3-ene-1-yl)-2,2-dimethyl-1,3-dioxypentane

E-(2R,3S,5ξ,8ξ)-3-O-benzyl-1,2-O-isopropylidene-6-nonen-1,2,3,5,8-pentaol

benzyl bromide

Downstream raw materials:

(2S)-2,4-dibenzyloxybutanal

(3S,4E)-1,3-di-O-benzylhex-4-ene-1,3,6-triol

(2S,4E)-1,3-di-O-benzyl-6-O-(methoxymethyl)hex-4-ene-1,3,6-triol

ethyl (2E,4S)-4,6-dibenzyloxyhex-2-enoate