Toluene-4-sulfonic acid (3aS,4S,6R,7R,7aS)-4-methoxy-7-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (3aS,4S,6R,7R,7aS)-4-methoxy-7-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethyl ester
• CAS No.: 182167-72-2
• Molecular Formula: C₂₅H₃₂O₉S
• Molecular Weight: 508.59
• Mol file: 182167-72-2.mol

Synonyms:Toluene-4-sulfonic acid (3aS,4S,6R,7R,7aS)-4-methoxy-7-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethyl ester

Chemical Property of Toluene-4-sulfonic acid (3aS,4S,6R,7R,7aS)-4-methoxy-7-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (3aS,4S,6R,7R,7aS)-4-methoxy-7-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethyl ester

There total 1 articles about Toluene-4-sulfonic acid (3aS,4S,6R,7R,7aS)-4-methoxy-7-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethyl ester 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: 90.0%

p-methoxybenzyl chloride (824-94-2) + methyl 2,3-O-isopropylidene-6-O-p-toluenesulfonyl-α-D-mannopyranoside (112612-45-0) → Toluene-4-sulfonic acid (3aS,4S,6R,7R,7aS)-4-methoxy-7-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethyl ester (182167-72-2)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; for 2h; Ambient temperature;

DOI:10.1080/07328309608005684

Reference yield: 75.0%

Toluene-4-sulfonic acid (3aS,4S,6R,7R,7aS)-4-methoxy-7-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethyl ester (182167-72-2) → Methyl 2,3-O-isopropylidene-4-O-(p-methoxybenzyl)-α-D-rhamnopyranoside (182167-71-1)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; for 2h; Heating;

DOI:10.1080/07328309608005684

Reference yield:

Toluene-4-sulfonic acid (3aS,4S,6R,7R,7aS)-4-methoxy-7-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethyl ester (182167-72-2) → Allyl 2-O-benzoyl-3-O-[2,4-di-O-benzoyl-3,6-dideoxy-4-O-(p-methoxybenzyl)-α-D-arabino-hexopyranosyl]-4,6-di-O-(p-methoxybenzyl)-α-D-mannopyranoside (182167-86-8)

Guidance literature:

Multi-step reaction with 10 steps

1: 75 percent / LiAlH₄ / diethyl ether / 2 h / Heating

2: 80 percent / 50percent aq. AcOH / 1 h / 60 °C

3: pyridine, SOCl₂ / ethyl acetate / 0.5 h / 0 °C

4: aq. NaIO₄, RuCl₃ / CH₂Cl₂; acetonitrile / 0.5 h / Ambient temperature

6: 93 percent / DDQ, H₂O / CH₂Cl₂ / 2 h / Ambient temperature

7: 95 percent / pyridine / 1 h / Ambient temperature

8: 84 percent / H₂SO₄ / 0.75 h / 0 °C

9: SnCl₄ / CH₂Cl₂ / 2 h / Ambient temperature

10: 93 percent / NIS, TfOH / 1,2-dichloro-ethane; diethyl ether / 0.25 h / -30 °C

With pyridine; ruthenium trichloride; sodium periodate; N-iodo-succinimide; lithium aluminium tetrahydride; thionyl chloride; trifluorormethanesulfonic acid; sulfuric acid; water; tin(IV) chloride; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In diethyl ether; dichloromethane; ethyl acetate; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1080/07328309608005684

upstream raw materials:

p-methoxybenzyl chloride

methyl 2,3-O-isopropylidene-6-O-p-toluenesulfonyl-α-D-mannopyranoside

Downstream raw materials:

Methyl 2,3-O-isopropylidene-4-O-(p-methoxybenzyl)-α-D-rhamnopyranoside

Methyl 2,4-di-O-benzoyl-3,6-dideoxy-α-D-arabino-hexopyranoside

Benzoic acid (2S,3S,5S,6R)-5-hydroxy-2-methoxy-6-methyl-tetrahydro-pyran-3-yl ester

Methyl 4-O-(p-methoxybenzyl)-α-D-rhamnopyranoside