(2R,3S)-1-benzyloxy-3,4-epoxy-2-(1'-methoxy-1'-methylaethoxy)-butan

Base Information

• Chemical Name: (2R,3S)-1-benzyloxy-3,4-epoxy-2-(1'-methoxy-1'-methylaethoxy)-butan
• CAS No.: 78469-92-8
• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.337
• Mol file: 78469-92-8.mol

Synonyms:

Chemical Property of (2R,3S)-1-benzyloxy-3,4-epoxy-2-(1'-methoxy-1'-methylaethoxy)-butan

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-1-benzyloxy-3,4-epoxy-2-(1'-methoxy-1'-methylaethoxy)-butan

There total 15 articles about (2R,3S)-1-benzyloxy-3,4-epoxy-2-(1'-methoxy-1'-methylaethoxy)-butan 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:

(4R,5R)-p-toluolsulfonsaeure<(5-benzyloxymethyl-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl)methyl>ester (78469-78-0) → (2R,3S)-1-benzyloxy-3,4-epoxy-2-(1'-methoxy-1'-methylaethoxy)-butan (78469-92-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) 2N HCl / 1.) THF, 15 h., 22 deg C, 2.) THF, methanol, 24 h., 22 deg C

2: Ba(OH)2*8H₂O / H₂O / Ambient temperature

3: 62 percent / triphenylphosphine, azodicarbonic acid diethylester / toluene / 1.) 15 min., -5 - 0 deg C, 2.) room temp., 8 h.

4: 96 percent / 1N KOH / tetrahydrofuran; methanol / 2.5 h / 10 - 15 °C

5: 1.) picric acid, 2.) Alox / 1.) methylene dichloride, 10 deg C, 20 min., 2.) 15 deg C, methylene dichloride, ether

With hydrogenchloride; barium dihydroxide; potassium hydroxide; diethyl azodicarbonate; 2,4,6-Trinitrophenol; triphenylphosphine; In tetrahydrofuran; methanol; water; toluene;

DOI:10.1002/hlca.19810640311

Reference yield:

benzyl bromide (100-39-0) → (2R,3S)-1-benzyloxy-3,4-epoxy-2-(1'-methoxy-1'-methylaethoxy)-butan (78469-92-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) NaH / 1.) DMF, -20 deg C, 20 min., 2.) DMF, 1 h., room temp.

2: 97 percent / pyridine / diethyl ether / 3 h / Ambient temperature

3: 1.) 2N HCl / 1.) THF, 15 h., 22 deg C, 2.) THF, methanol, 24 h., 22 deg C

4: Ba(OH)2*8H₂O / H₂O / Ambient temperature

5: 62 percent / triphenylphosphine, azodicarbonic acid diethylester / toluene / 1.) 15 min., -5 - 0 deg C, 2.) room temp., 8 h.

6: 96 percent / 1N KOH / tetrahydrofuran; methanol / 2.5 h / 10 - 15 °C

7: 1.) picric acid, 2.) Alox / 1.) methylene dichloride, 10 deg C, 20 min., 2.) 15 deg C, methylene dichloride, ether

With pyridine; hydrogenchloride; barium dihydroxide; potassium hydroxide; diethyl azodicarbonate; sodium hydride; 2,4,6-Trinitrophenol; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; water; toluene;

DOI:10.1002/hlca.19810640311

Reference yield:

1-O-benzyl-2,3-O-isopropylidene-D-threitol (78469-77-9) → (2R,3S)-1-benzyloxy-3,4-epoxy-2-(1'-methoxy-1'-methylaethoxy)-butan (78469-92-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 97 percent / pyridine / diethyl ether / 3 h / Ambient temperature

2: 1.) 2N HCl / 1.) THF, 15 h., 22 deg C, 2.) THF, methanol, 24 h., 22 deg C

3: Ba(OH)2*8H₂O / H₂O / Ambient temperature

4: 62 percent / triphenylphosphine, azodicarbonic acid diethylester / toluene / 1.) 15 min., -5 - 0 deg C, 2.) room temp., 8 h.

5: 96 percent / 1N KOH / tetrahydrofuran; methanol / 2.5 h / 10 - 15 °C

6: 1.) picric acid, 2.) Alox / 1.) methylene dichloride, 10 deg C, 20 min., 2.) 15 deg C, methylene dichloride, ether

With pyridine; hydrogenchloride; barium dihydroxide; potassium hydroxide; diethyl azodicarbonate; 2,4,6-Trinitrophenol; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; water; toluene;

DOI:10.1002/hlca.19810640311

upstream raw materials:

2-Methoxypropene

(2S,3R)-1-benzyloxy-3,4-epoxy-2-butanol

(4R,5R)-p-toluolsulfonsaeure<(5-benzyloxymethyl-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl)methyl>ester

benzyl bromide

Downstream raw materials:

(4R,5S)-6-benzyloxy-4,5-isopropylidenedioxy-2-hexanone

(2R,3S)-2-<4-benzyloxy-2,3-(isopropylidenedioxy)butyl>-2-methyl-1,3-dithiane

Refernces

• 1、 Hungerbuehler, Ernst,Seebach, Dieter. "Chiral Electrophilic Synthetic Building Blocks with Four Different Functional Groups from Tartaric Acid, 2,3- and 3,4-Epoxy-butanediol Derivatives in All Four Stereoisomeric Forms". . p. 687 - 702. Retrieved 2007/10/02.