Toluene-4-sulfonic acid (2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-3-(4-methoxy-benzyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-3-(4-methoxy-benzyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 199792-21-7
• Molecular Formula: C₄₅H₅₀O₁₀S
• Molecular Weight: 782.952

Synonyms:Toluene-4-sulfonic acid (2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-3-(4-methoxy-benzyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-tetrahydro-pyran-2-ylmethyl ester

Chemical Property of Toluene-4-sulfonic acid (2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-3-(4-methoxy-benzyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-tetrahydro-pyran-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-3-(4-methoxy-benzyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-tetrahydro-pyran-2-ylmethyl ester

There total 13 articles about Toluene-4-sulfonic acid (2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-3-(4-methoxy-benzyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-tetrahydro-pyran-2-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: 100.0%

p-toluenesulfonyl chloride (98-59-9) + {(2R,3R,4R,5S,6S)-4,5-Bis-benzyloxy-3-(4-methoxy-benzyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-tetrahydro-pyran-2-yl}-methanol (199791-98-5) → Toluene-4-sulfonic acid (2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-3-(4-methoxy-benzyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-tetrahydro-pyran-2-ylmethyl ester (199792-21-7)

Guidance literature:

With dmap; triethylamine; In dichloromethane; for 6h; Ambient temperature;

DOI:10.1016/S0040-4020(97)10254-X

Reference yield:

allyl 2,3-O-dibenzyl-4,6-O-p-methoxybenzylidene-D-glucopyranoside (199791-95-2) → Toluene-4-sulfonic acid (2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-3-(4-methoxy-benzyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-tetrahydro-pyran-2-ylmethyl ester (199792-21-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 1) i-Pr₂NEt, (Ph₃P)3RhCl, 2) HgO, HgCl₂ / 1) EtOH, reflux, 2 h, 2) acetone, H₂O, room temperature, 1 h

2: 99 percent / benzene / 24 h / Heating

3: 100 percent / NaH / tetrahydrofuran / 16 h / Ambient temperature

4: 98 percent / LiAlH₄ / diethyl ether; tetrahydrofuran / 0.5 h / 0 °C

5: 100 percent / KH / tetrahydrofuran / 3 h / Ambient temperature

6: 95 percent / DIBAL / CH₂Cl₂; hexane / 1) -78 deg C -> 0 deg C, 2) 0 deg C, 40 min

7: 100 percent / NEt₃, DMAP / CH₂Cl₂ / 6 h / Ambient temperature

With dmap; Wilkinson's catalyst; lithium aluminium tetrahydride; potassium hydride; sodium hydride; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; benzene;

DOI:10.1016/S0040-4020(97)10254-X

Reference yield:

[(4aR,6S,7S,8R,8aR)-7,8-Bis-benzyloxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-acetic acid methyl ester (199791-97-4) → Toluene-4-sulfonic acid (2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-3-(4-methoxy-benzyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-tetrahydro-pyran-2-ylmethyl ester (199792-21-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / LiAlH₄ / diethyl ether; tetrahydrofuran / 0.5 h / 0 °C

2: 100 percent / KH / tetrahydrofuran / 3 h / Ambient temperature

3: 95 percent / DIBAL / CH₂Cl₂; hexane / 1) -78 deg C -> 0 deg C, 2) 0 deg C, 40 min

4: 100 percent / NEt₃, DMAP / CH₂Cl₂ / 6 h / Ambient temperature

With dmap; lithium aluminium tetrahydride; potassium hydride; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;

DOI:10.1016/S0040-4020(97)10254-X

upstream raw materials:

p-toluenesulfonyl chloride

{(2R,3R,4R,5S,6S)-4,5-Bis-benzyloxy-3-(4-methoxy-benzyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-tetrahydro-pyran-2-yl}-methanol

p-methoxybenzyl chloride

allyl 2,3-O-dibenzyl-4,6-O-p-methoxybenzylidene-D-glucopyranoside

Downstream raw materials:

{(2R,3R,4S,5S,6S)-4,5-Bis-benzyloxy-3-(4-methoxy-benzyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-tetrahydro-pyran-2-yl}-acetonitrile

(2S,3S,4R,4aR,6R,7S,8aR)-4-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-(2-iodo-ethyl)-octahydro-pyrano[3,2-b]pyran-3-ol

(2S,3S,4R,4aR,6R,7S,8aR)-4-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-(2-hydroxy-ethyl)-octahydro-pyrano[3,2-b]pyran-3-ol

2-{(2R,3S,4aR,6S,7S,8R,8aR)-7,8-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-octahydro-pyrano[3,2-b]pyran-2-yl}-ethanol

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