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

Base Information

• Chemical Name: Benzoic acid (1S,2R,3R,4R,5S,6R)-3,4-bis-benzyloxy-5-[1,3]dithian-2-yl-6-ethoxycarbonylmethyl-2-hydroxy-cyclohexyl ester
• CAS No.: 120927-71-1
• Molecular Formula: C₃₅H₄₀O₇S₂
• Molecular Weight: 636.83

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

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

Chemical Property:

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

There total 6 articles about Benzoic acid (1S,2R,3R,4R,5S,6R)-3,4-bis-benzyloxy-5-[1,3]dithian-2-yl-6-ethoxycarbonylmethyl-2-hydroxy-cyclohexyl 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: 63.0%

1.3-propanedithiol (109-80-8) + [(1S,3R,4R,5R,6S,7S,8R)-7,8-Bis-benzyloxy-6-hydroxy-3-(4-methoxy-phenoxy)-2-oxa-bicyclo[2.2.2]oct-5-yl]-acetic acid ethyl ester → 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:

With boron trifluoride diethyl etherate;

DOI:10.1021/jo00271a005

Reference yield: 62.0%

1.3-propanedithiol (109-80-8) + Benzoic acid (1R,3S,4S,5R,6S,7S,8R)-7,8-bis-benzyloxy-5-ethoxycarbonylmethyl-3-(4-methoxy-benzyloxy)-2-oxa-bicyclo[2.2.2]oct-6-yl ester (120927-70-0) → 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:

With boron trifluoride diethyl etherate; In dichloromethane; 1) -15 deg C, 2) 0 deg C, 30 min;

DOI:10.1021/jo00028a033

Reference yield:

benzoyl chloride (98-88-4) → 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

upstream raw materials:

1.3-propanedithiol

Benzoic acid (1R,3S,4S,5R,6S,7S,8R)-7,8-bis-benzyloxy-5-ethoxycarbonylmethyl-3-(4-methoxy-benzyloxy)-2-oxa-bicyclo[2.2.2]oct-6-yl ester

benzoyl chloride

[(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

Downstream raw materials:

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

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