1,6-anhydro-2-desoxy-2,4-di-C-methyl-3-O-(4-methoxybenzyl)-β-D-galactopyranose

Base Information

• Chemical Name: 1,6-anhydro-2-desoxy-2,4-di-C-methyl-3-O-(4-methoxybenzyl)-β-D-galactopyranose
• CAS No.: 123493-66-3
• Molecular Formula: C₁₆H₂₂O₅
• Molecular Weight: 294.348
• Mol file: 123493-66-3.mol

Synonyms:1,6-anhydro-2-desoxy-2,4-di-C-methyl-3-O-(4-methoxybenzyl)-β-D-galactopyranose

Chemical Property of 1,6-anhydro-2-desoxy-2,4-di-C-methyl-3-O-(4-methoxybenzyl)-β-D-galactopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,6-anhydro-2-desoxy-2,4-di-C-methyl-3-O-(4-methoxybenzyl)-β-D-galactopyranose

There total 7 articles about 1,6-anhydro-2-desoxy-2,4-di-C-methyl-3-O-(4-methoxybenzyl)-β-D-galactopyranose 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: 98.0%

methylmagnesium bromide (75-16-1) + 1,6-anhydro-2-desoxy-2-C-methyl-3-O-(4-methoxybenzyl)-β-D-xylo-hexapyranoz-4-ylose (123493-65-2) → 1,6-anhydro-2-desoxy-2,4-di-C-methyl-3-O-(4-methoxybenzyl)-β-D-galactopyranose (123493-66-3)

Guidance literature:

In tetrahydrofuran; at -40 ℃; for 0.166667h;

DOI:10.1016/S0040-4020(01)96139-3

Reference yield: 98.0%

1,6-anhydro-2-desoxy-2-C-methyl-3-O-(4-methoxybenzyl)-β-D-xylo-hexapyranoz-4-ylose (123493-65-2) + methylmagnesium chloride (676-58-4) → 1,6-anhydro-2-desoxy-2,4-di-C-methyl-3-O-(4-methoxybenzyl)-β-D-galactopyranose (123493-66-3)

Guidance literature:

In tetrahydrofuran; at -40 ℃; for 0.166667h;

DOI:10.1007/BF00958057

Reference yield:

4-O-allyl-1,6-anhydro-2-deoxy-2-C-methyl-β-D-glucopyranose (91510-64-4) → 1,6-anhydro-2-desoxy-2,4-di-C-methyl-3-O-(4-methoxybenzyl)-β-D-galactopyranose (123493-66-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) NaH / 1) DMF, 1.5 h, 2) 2.5 h

2: 1) t-BuOK, 2) Hg(OAc)2 / 1) DMSO, 2 h, 2) acetone, H₂O, 10 min

3: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -60 deg C, 25 min, 2) -60 deg C up to 0 deg C, 3 min

4: 98 percent / tetrahydrofuran / 0.17 h / -40 °C

With oxalyl dichloride; potassium tert-butylate; mercury(II) diacetate; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran;

DOI:10.1016/S0040-4020(01)96139-3

upstream raw materials:

1,6-anhydro-2-desoxy-2-C-methyl-3-O-(4-methoxybenzyl)-β-D-xylo-hexapyranoz-4-ylose

methylmagnesium chloride

methylmagnesium bromide

4-O-allyl-1,6-anhydro-2-deoxy-2-C-methyl-β-D-glucopyranose

Downstream raw materials:

Dithiocarbonic acid O-((1R,2R,3R,4R,5R)-2-benzyloxy-2,4-dimethyl-6,8-dioxa-bicyclo[3.2.1]oct-3-yl) ester S-methyl ester

((2R,3R,5R,6S)-3-Benzyloxy-6-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-methanol

((2R,3R,5R,6R)-3-Benzyloxy-6-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-methanol

{(2R,4R)-4-Benzyloxy-4-[(2R,4R,5S,6R)-2-(4-methoxy-phenyl)-5-methyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-2-methyl-pentyloxy}-tert-butyl-dimethyl-silane