[(1R,3S,4S,5R,6S,7S,8R)-7,8-Bis-benzyloxy-6-hydroxy-3-(4-methoxy-benzyloxy)-2-oxa-bicyclo[2.2.2]oct-5-yl]-acetic acid ethyl ester

Base Information

• Chemical Name: [(1R,3S,4S,5R,6S,7S,8R)-7,8-Bis-benzyloxy-6-hydroxy-3-(4-methoxy-benzyloxy)-2-oxa-bicyclo[2.2.2]oct-5-yl]-acetic acid ethyl ester
• CAS No.: 120964-43-4
• Molecular Formula: C₃₃H₃₈O₈
• Molecular Weight: 562.66
• Mol file: 120964-43-4.mol

Synonyms:[(1R,3S,4S,5R,6S,7S,8R)-7,8-Bis-benzyloxy-6-hydroxy-3-(4-methoxy-benzyloxy)-2-oxa-bicyclo[2.2.2]oct-5-yl]-acetic acid ethyl ester

Chemical Property of [(1R,3S,4S,5R,6S,7S,8R)-7,8-Bis-benzyloxy-6-hydroxy-3-(4-methoxy-benzyloxy)-2-oxa-bicyclo[2.2.2]oct-5-yl]-acetic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(1R,3S,4S,5R,6S,7S,8R)-7,8-Bis-benzyloxy-6-hydroxy-3-(4-methoxy-benzyloxy)-2-oxa-bicyclo[2.2.2]oct-5-yl]-acetic acid ethyl ester

There total 1 articles about [(1R,3S,4S,5R,6S,7S,8R)-7,8-Bis-benzyloxy-6-hydroxy-3-(4-methoxy-benzyloxy)-2-oxa-bicyclo[2.2.2]oct-5-yl]-acetic acid ethyl 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: 66.0%

[(1S,3S,4S,6S,7S,8R)-7,8-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2-oxa-bicyclo[2.2.2]oct-5-yl]-acetic acid ethyl ester (120927-67-5,120964-40-1,120964-41-2,120964-42-3) → (1R,2S,6S,7S,8S,10S,11R)-10,11-Bis-benzyloxy-8-(4-methoxy-benzyloxy)-3,9-dioxa-tricyclo[5.2.2.02,6]undecan-4-one (120927-68-6,120964-44-5) + [(1R,3S,4S,5R,6S,7S,8R)-7,8-Bis-benzyloxy-6-hydroxy-3-(4-methoxy-benzyloxy)-2-oxa-bicyclo[2.2.2]oct-5-yl]-acetic acid ethyl ester (120964-43-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 4h; Ambient temperature;

DOI:10.1021/jo00028a033

Reference yield:

[(1R,3S,4S,5R,6S,7S,8R)-7,8-Bis-benzyloxy-6-hydroxy-3-(4-methoxy-benzyloxy)-2-oxa-bicyclo[2.2.2]oct-5-yl]-acetic acid ethyl ester (120964-43-4) → Benzoic acid (1S,2R,3R,4R,5S,6R)-3,4-bis-benzyloxy-5-[1,3]dithian-2-yl-6-ethoxycarbonylmethyl-2-hydroxy-cyclohexyl ester (120927-71-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / pyridine / 1) 0 deg C, 1 h, 2) rt, 2 h

2: 62 percent / BF₃*Et₂O / CH₂Cl₂ / 1) -15 deg C, 2) 0 deg C, 30 min

With pyridine; boron trifluoride diethyl etherate; In dichloromethane;

DOI:10.1021/jo00028a033

Reference yield:

[(1R,3S,4S,5R,6S,7S,8R)-7,8-Bis-benzyloxy-6-hydroxy-3-(4-methoxy-benzyloxy)-2-oxa-bicyclo[2.2.2]oct-5-yl]-acetic acid ethyl ester (120964-43-4) → Ethyl 6-(Benzoyloxy)-3,4-bis(benzyloxy)-5-hydroxy-2-<2-(1,3-dithianyl)>cyclohex-1-ylacetate (120927-72-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / pyridine / 1) 0 deg C, 1 h, 2) rt, 2 h

2: 62 percent / BF₃*Et₂O / CH₂Cl₂ / 1) -15 deg C, 2) 0 deg C, 30 min

3: DMAP / ethyl acetate

With pyridine; dmap; boron trifluoride diethyl etherate; In dichloromethane; ethyl acetate;

DOI:10.1021/jo00028a033

upstream raw materials:

[(1S,3S,4S,6S,7S,8R)-7,8-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2-oxa-bicyclo[2.2.2]oct-5-yl]-acetic acid ethyl ester

Downstream raw materials:

Benzoic acid (1S,2R,3R,4R,5S,6R)-3,4-bis-benzyloxy-5-[1,3]dithian-2-yl-6-ethoxycarbonylmethyl-2-hydroxy-cyclohexyl ester

Ethyl 6-(Benzoyloxy)-3,4-bis(benzyloxy)-5-hydroxy-2-<2-(1,3-dithianyl)>cyclohex-1-ylacetate