(2S,3R)-2-Methyl-3-((2R,4S,5R)-5-methyl-2-phenyl-5-trimethylsilanyloxy-[1,3]dioxan-4-ylmethyl)-oxirane-2-carbaldehyde

Base Information

• Chemical Name: (2S,3R)-2-Methyl-3-((2R,4S,5R)-5-methyl-2-phenyl-5-trimethylsilanyloxy-[1,3]dioxan-4-ylmethyl)-oxirane-2-carbaldehyde
• CAS No.: 131310-99-1
• Molecular Formula: C₁₉H₂₈O₅Si
• Molecular Weight: 364.514

Synonyms:(2S,3R)-2-Methyl-3-((2R,4S,5R)-5-methyl-2-phenyl-5-trimethylsilanyloxy-[1,3]dioxan-4-ylmethyl)-oxirane-2-carbaldehyde

Chemical Property of (2S,3R)-2-Methyl-3-((2R,4S,5R)-5-methyl-2-phenyl-5-trimethylsilanyloxy-[1,3]dioxan-4-ylmethyl)-oxirane-2-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-2-Methyl-3-((2R,4S,5R)-5-methyl-2-phenyl-5-trimethylsilanyloxy-[1,3]dioxan-4-ylmethyl)-oxirane-2-carbaldehyde

There total 9 articles about (2S,3R)-2-Methyl-3-((2R,4S,5R)-5-methyl-2-phenyl-5-trimethylsilanyloxy-[1,3]dioxan-4-ylmethyl)-oxirane-2-carbaldehyde 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: 93.0%

[(2R,3R)-2-Methyl-3-((2R,4S,5R)-5-methyl-2-phenyl-5-trimethylsilanyloxy-[1,3]dioxan-4-ylmethyl)-oxiranyl]-methanol (131310-98-0) → (2S,3R)-2-Methyl-3-((2R,4S,5R)-5-methyl-2-phenyl-5-trimethylsilanyloxy-[1,3]dioxan-4-ylmethyl)-oxirane-2-carbaldehyde (131310-99-1)

Guidance literature:

With pyridine-SO₃ complex; triethylamine; In dichloromethane; dimethyl sulfoxide; at 0 ℃; for 2h;

DOI:10.1016/S0040-4020(01)85579-4

Reference yield:

2-deoxy-D-ribose (22900-10-3,35536-75-5,36792-85-5,113890-34-9,113890-37-2,133813-23-7) → (2S,3R)-2-Methyl-3-((2R,4S,5R)-5-methyl-2-phenyl-5-trimethylsilanyloxy-[1,3]dioxan-4-ylmethyl)-oxirane-2-carbaldehyde (131310-99-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 97 percent / tetrahydrofuran / 3 h / Heating

2: 96 percent / camphorsulfonic acid / CH₂Cl₂ / 12 h / 25 °C

3: 89 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 1 h / -78 °C

4: 84 percent / hexane; CH₂Cl₂ / 2 h / -20 °C

5: 100 percent / CH₂Cl₂ / 0.25 h / 25 °C

6: 96 percent / DIBAL / CH₂Cl₂ / 0.25 h / -78 °C

7: 1.) diethyl-D-tartrate, titanium(IV) isopropoxide, 2.) tert-butylhydroperoxide / 1.) CH₂Cl₂, -25 deg C, 30 min, 2.) 2,2,4-trimethylpentane, -20 deg C, 14 h

8: 93 percent / triethylamine, SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / 2 h / 0 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; oxalyl dichloride; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; camphor-10-sulfonic acid; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide;

DOI:10.1016/S0040-4020(01)85579-4

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → (2S,3R)-2-Methyl-3-((2R,4S,5R)-5-methyl-2-phenyl-5-trimethylsilanyloxy-[1,3]dioxan-4-ylmethyl)-oxirane-2-carbaldehyde (131310-99-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 96 percent / camphorsulfonic acid / CH₂Cl₂ / 12 h / 25 °C

2: 89 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 1 h / -78 °C

3: 84 percent / hexane; CH₂Cl₂ / 2 h / -20 °C

4: 100 percent / CH₂Cl₂ / 0.25 h / 25 °C

5: 96 percent / DIBAL / CH₂Cl₂ / 0.25 h / -78 °C

6: 1.) diethyl-D-tartrate, titanium(IV) isopropoxide, 2.) tert-butylhydroperoxide / 1.) CH₂Cl₂, -25 deg C, 30 min, 2.) 2,2,4-trimethylpentane, -20 deg C, 14 h

7: 93 percent / triethylamine, SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / 2 h / 0 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; oxalyl dichloride; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; camphor-10-sulfonic acid; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In hexane; dichloromethane; dimethyl sulfoxide;

DOI:10.1016/S0040-4020(01)85579-4

upstream raw materials:

[(2R,3R)-2-Methyl-3-((2R,4S,5R)-5-methyl-2-phenyl-5-trimethylsilanyloxy-[1,3]dioxan-4-ylmethyl)-oxiranyl]-methanol

2-deoxy-D-ribose

benzaldehyde dimethyl acetal

(E)-(5S,6R)-5,6,7-Trihydroxy-2-methyl-hept-2-enoic acid ethyl ester

Downstream raw materials:

Trimethyl-[(2R,4S,5R)-5-methyl-4-((2R,3R)-3-methyl-3-vinyl-oxiranylmethyl)-2-phenyl-[1,3]dioxan-5-yloxy]-silane

(2R,4S,5R)-5-Methyl-4-((2R,3R)-3-methyl-3-vinyl-oxiranylmethyl)-2-phenyl-[1,3]dioxan-5-ol

(2R,4aR,6S,7R,8aS)-4a,6-Dimethyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

(2R,4aR,6S,7R,8aS)-4a,6-Dimethyl-6-((2R,3R)-3-methyl-3-vinyl-oxiranylmethyl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

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