methyl 2,4-dideoxy-2,4-di-C-methyl-6-O-trityl-α-D-talopyranoside

Base Information

• Chemical Name: methyl 2,4-dideoxy-2,4-di-C-methyl-6-O-trityl-α-D-talopyranoside
• CAS No.: 118360-86-4
• Molecular Formula: C₂₈H₃₂O₄
• Molecular Weight: 432.56
• Mol file: 118360-86-4.mol

Synonyms:

Chemical Property of methyl 2,4-dideoxy-2,4-di-C-methyl-6-O-trityl-α-D-talopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,4-dideoxy-2,4-di-C-methyl-6-O-trityl-α-D-talopyranoside

There total 16 articles about methyl 2,4-dideoxy-2,4-di-C-methyl-6-O-trityl-α-D-talopyranoside 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:

methyl 2,3-anhydro-4,6-O-benzylidene-α-D-allopyranoside (2880-96-8,3150-15-0,3150-16-1,3257-59-8,14187-71-4,15384-57-3,19465-13-5,32976-15-1,52885-37-7,53270-02-3,53270-03-4,65391-11-9,65391-12-0,66537-92-6,67226-04-4,71184-14-0,86420-78-2,86420-79-3,91177-51-4,91177-52-5,117708-93-7,120408-72-2) → (2S,3R,5S,6S)-2-Methoxy-3,5-dimethyl-6-trityloxymethyl-tetrahydro-pyran-4-ol (109914-99-0,109915-00-6,118360-86-4)

Guidance literature:

Multi-step reaction with 9 steps

1: 56 percent / Cu(I)I / diethyl ether / 5 h / 0 °C

2: 94 percent / NaH / tetrahydrofuran / 18 h / Heating

3: 85 percent / toluene-p-sulphonic acid monohydrate / methanol / 3 h / 0 °C

4: 95 percent / pyridine / 70 °C

5: oxalylchloride, DMSO / CH₂Cl₂ / 4 h / -60 °C

6: 84 percent / n-butyl-lithium / diethyl ether; hexane / 2 h / Heating

7: 35 percent / H₂ / 10percent Pd-C / ethyl acetate / 1 h / 50 °C

8: 62 percent / DMSO, oxalyl chloride / CH₂Cl₂ / 2 h / -60 °C

9: 1.) sodium methoxide, 2.) sodium borohydride / 1.) methanol, 12h, -30 deg C; 2.) methanol, 30 min

With sodium tetrahydroborate; copper(l) iodide; n-butyllithium; oxalyl dichloride; Chloro-oxo-acetic acid; hydrogen; sodium methylate; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; diethyl ether; hexane; dichloromethane; ethyl acetate;

Reference yield:

methyl 3-O-benzyl-2,4-dideoxy-2-C-methyl-4-C-methylene-6-O-trityl-α-D-arabino-hexopyranoside (109914-96-7) → (2S,3R,5S,6S)-2-Methoxy-3,5-dimethyl-6-trityloxymethyl-tetrahydro-pyran-4-ol (109914-99-0,109915-00-6,118360-86-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 35 percent / H₂ / 10percent Pd-C / ethyl acetate / 1 h / 50 °C

2: 62 percent / DMSO, oxalyl chloride / CH₂Cl₂ / 2 h / -60 °C

3: 1.) sodium methoxide, 2.) sodium borohydride / 1.) methanol, 12h, -30 deg C; 2.) methanol, 30 min

With sodium tetrahydroborate; oxalyl dichloride; hydrogen; sodium methylate; dimethyl sulfoxide; palladium on activated charcoal; In dichloromethane; ethyl acetate;

Reference yield:

methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-C-methyl-α-D-altropyranoside (75837-44-4,109958-35-2,121467-57-0) → (2S,3R,5S,6S)-2-Methoxy-3,5-dimethyl-6-trityloxymethyl-tetrahydro-pyran-4-ol (109914-99-0,109915-00-6,118360-86-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 85 percent / toluene-p-sulphonic acid monohydrate / methanol / 3 h / 0 °C

2: 95 percent / pyridine / 70 °C

3: oxalylchloride, DMSO / CH₂Cl₂ / 4 h / -60 °C

4: 84 percent / n-butyl-lithium / diethyl ether; hexane / 2 h / Heating

5: 35 percent / H₂ / 10percent Pd-C / ethyl acetate / 1 h / 50 °C

6: 62 percent / DMSO, oxalyl chloride / CH₂Cl₂ / 2 h / -60 °C

7: 1.) sodium methoxide, 2.) sodium borohydride / 1.) methanol, 12h, -30 deg C; 2.) methanol, 30 min

With sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; Chloro-oxo-acetic acid; hydrogen; sodium methylate; toluene-4-sulfonic acid; dimethyl sulfoxide; palladium on activated charcoal; In pyridine; methanol; diethyl ether; hexane; dichloromethane; ethyl acetate;

upstream raw materials:

methyl 2,4-dideoxy-2,4-di-C-methyl-6-O-trityl-α-D-lyxopyranosid-3-ulose

methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-C-methyl-α-D-altropyranoside

methyl 3-O-benzyl-2,4-dideoxy-2-C-methyl-4-C-methylene-6-O-trityl-α-D-arabino-hexopyranoside

methyl 3-O-benzyl-2-deoxy-2-C-methyl-6-O-trityl-α-D-altropyranoside

Downstream raw materials:

methyl 2,3,4-trideoxy-2,4-di-C-methyl-6-O-(triphenylmethyl)-α-D-arabino-hexopyranoside

methyl 2,3,4-trideoxy-2,3-di-C-methyl-6-O-trityl-α-D-ribo-hexopyranoside