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

Base Information

• Chemical Name: methyl 2,3,4-trideoxy-2,3-di-C-methyl-6-O-trityl-α-D-ribo-hexopyranoside
• CAS No.: 79646-63-2
• Molecular Formula: C₂₈H₃₂O₃
• Molecular Weight: 416.56
• Mol file: 79646-63-2.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 21 articles about methyl 2,3,4-trideoxy-2,3-di-C-methyl-6-O-trityl-α-D-ribo-hexopyranoside 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) → methyl 2,3,4-trideoxy-2,3-di-C-methyl-6-O-trityl-α-D-ribo-hexopyranoside (79646-63-2)

Guidance literature:

Multi-step reaction with 10 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

10: 1.) NaH, CS₂, iodomethane, 2.) tri- n-butyltin hydride, azaisobutyronitrile / 1.) THF, 35 deg C, 4 h; 2.) toluene, reflux, 2 h

With carbon disulfide; sodium tetrahydroborate; copper(l) iodide; n-butyllithium; oxalyl dichloride; Chloro-oxo-acetic acid; hydrogen; tri-n-butyl-tin hydride; sodium methylate; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; NCNMe₂; methyl iodide; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; diethyl ether; hexane; dichloromethane; ethyl acetate;

Reference yield:

methyl 3,4-dideoxy-4-c-methyl-6-o-trityl-α-D-glycero-hex-3-enopyranosid-2-ulose (79607-37-7) → methyl 2,3,4-trideoxy-2,3-di-C-methyl-6-O-trityl-α-D-ribo-hexopyranoside (79646-63-2)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂ / Pd

3: H₂ / Pd

With hydrogen; palladium;

DOI:10.1016/S0040-4039(01)90512-X

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) → methyl 2,3,4-trideoxy-2,3-di-C-methyl-6-O-trityl-α-D-ribo-hexopyranoside (79646-63-2)

Guidance literature:

Multi-step reaction with 8 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

8: 1.) NaH, CS₂, iodomethane, 2.) tri- n-butyltin hydride, azaisobutyronitrile / 1.) THF, 35 deg C, 4 h; 2.) toluene, reflux, 2 h

With carbon disulfide; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; Chloro-oxo-acetic acid; hydrogen; tri-n-butyl-tin hydride; sodium methylate; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; NCNMe₂; methyl iodide; palladium on activated charcoal; In pyridine; methanol; diethyl ether; hexane; dichloromethane; ethyl acetate;

upstream raw materials:

(2S,3R,6S)-2-Methoxy-3-methyl-5-methylene-6-trityloxymethyl-tetrahydro-pyran

(2S,6S)-2-Methoxy-5-methyl-3-methylene-6-trityloxymethyl-3,6-dihydro-2H-pyran

(2S,5S,6S)-2-Methoxy-5-methyl-3-methylene-6-trityloxymethyl-tetrahydro-pyran

(2S,3R,5S,6S)-2-Methoxy-3,5-dimethyl-6-trityloxymethyl-tetrahydro-pyran-4-ol

Downstream raw materials:

Toluene-4-sulfonic acid (1S,2S,4R)-1-(tert-butyl-dimethyl-silanyloxymethyl)-4-[1,3]dithian-2-yl-2-methyl-pentyl ester