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

Base Information

• Chemical Name: {(2R,3R,4R,5S,6S)-4,5-Bis-benzyloxy-3-(4-methoxy-benzyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-tetrahydro-pyran-2-yl}-methanol
• CAS No.: 199791-98-5
• Molecular Formula: C₃₈H₄₄O₈
• Molecular Weight: 628.763

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 12 articles about {(2R,3R,4R,5S,6S)-4,5-Bis-benzyloxy-3-(4-methoxy-benzyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-tetrahydro-pyran-2-yl}-methanol 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: 95.0%

(4aR,6S,7S,8R,8aR)-7,8-Bis-benzyloxy-6-[2-(4-methoxy-benzyloxy)-ethyl]-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine (199792-20-6) → {(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)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1016/S0040-4039(97)10107-1

Reference yield:

allyl 2,3-O-dibenzyl-4,6-O-p-methoxybenzylidene-D-glucopyranoside (199791-95-2) → {(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)

Guidance literature:

Multi-step reaction with 6 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

With Wilkinson's catalyst; lithium aluminium tetrahydride; potassium hydride; sodium hydride; diisobutylaluminium hydride; 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) → {(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)

Guidance literature:

Multi-step reaction with 3 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

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

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

upstream raw materials:

(4aR,6S,7S,8R,8aR)-7,8-Bis-benzyloxy-6-[2-(4-methoxy-benzyloxy)-ethyl]-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine

p-methoxybenzyl chloride

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

2-[(4aR,6S,7S,8R,8aR)-7,8-Bis-benzyloxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-ethanol

Downstream raw materials:

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

(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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