(2S,3R)-1,4-Bis-benzyloxy-2-((1R,4R,5R,6S)-6-benzyloxy-1-ethyl-5-hydroxy-2,7-dioxa-bicyclo[2.2.1]hept-4-yl)-butane-2,3-diol

Base Information

Chemical Name:(2S,3R)-1,4-Bis-benzyloxy-2-((1R,4R,5R,6S)-6-benzyloxy-1-ethyl-5-hydroxy-2,7-dioxa-bicyclo[2.2.1]hept-4-yl)-butane-2,3-diol
CAS No.:185757-76-0
Molecular Formula:C₃₂H₃₈O₈
Molecular Weight:550.649
Hs Code.:

Synonyms:(2S,3R)-1,4-Bis-benzyloxy-2-((1R,4R,5R,6S)-6-benzyloxy-1-ethyl-5-hydroxy-2,7-dioxa-bicyclo[2.2.1]hept-4-yl)-butane-2,3-diol

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Chemical Property of (2S,3R)-1,4-Bis-benzyloxy-2-((1R,4R,5R,6S)-6-benzyloxy-1-ethyl-5-hydroxy-2,7-dioxa-bicyclo[2.2.1]hept-4-yl)-butane-2,3-diol

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Technology Process of (2S,3R)-1,4-Bis-benzyloxy-2-((1R,4R,5R,6S)-6-benzyloxy-1-ethyl-5-hydroxy-2,7-dioxa-bicyclo[2.2.1]hept-4-yl)-butane-2,3-diol

There total 15 articles about (2S,3R)-1,4-Bis-benzyloxy-2-((1R,4R,5R,6S)-6-benzyloxy-1-ethyl-5-hydroxy-2,7-dioxa-bicyclo[2.2.1]hept-4-yl)-butane-2,3-diol 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%

: 185757-75-9
(1R,2S)-2-Benzyloxy-1-[(S)-2-((1S,2R)-3-benzyloxy-1-benzyloxymethyl-1,2-dihydroxy-propyl)-oxiranyl]-1-hydroxy-pentan-3-one

: 185757-76-0
(2S,3R)-1,4-Bis-benzyloxy-2-((1R,4R,5R,6S)-6-benzyloxy-1-ethyl-5-hydroxy-2,7-dioxa-bicyclo[2.2.1]hept-4-yl)-butane-2,3-diol

Guidance literature:: With pyridinium p-toluenesulfonate; In methanol; at 20 ℃; for 2h;
DOI:10.1016/S0040-4039(96)02083-7

Reference yield:

: 68972-96-3
(Z)-1,4-dibenzyloxy-2-butene

: 185757-76-0
(2S,3R)-1,4-Bis-benzyloxy-2-((1R,4R,5R,6S)-6-benzyloxy-1-ethyl-5-hydroxy-2,7-dioxa-bicyclo[2.2.1]hept-4-yl)-butane-2,3-diol

Guidance literature:: Multi-step reaction with 13 steps

1: I₂ / CH₂Cl₂

2: 1.) n-BuLi, 2.) ZnBr₂, 3.) Pd(MeCN)2Cl₂ / 1.) THF, -78 deg C, 30 min, 2.) 2.5 h, 3.) DMF, from -78 deg C to 20 deg C, 2 h

3: 1M HCl / tetrahydrofuran / 4 h / 20 °C

4: 1.) (c-C₆H₁₁)2BCl, Et₃N, Me₂NEt, 3.) H₂O₂ / 1.) Et₂O, 0 deg C, 3 h, 2.) from -78 deg C to -18 deg C, 18 h, 3.) MeOH, pH 7 buffer

5: 76 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

6: 73 percent / LiBH₄ / tetrahydrofuran / 36 h / -78 - 20 °C

7: 82 percent / NaIO₄ / methanol / 1 h / 20 °C / pH 6.5 buffer

8: tetrahydrofuran / 2 h / -78 - 0 °C

9: TPAP, NMO / CH₂Cl₂ / 6 h / 20 °C

10: 88 percent / HF*py / pyridine; tetrahydrofuran

11: 61 percent / (DHQD)2PHAL, K₂OsO₄*2H₂O, NaHCO₃ / 2-methyl-propan-2-ol; H₂O / 14 h / 20 °C

12: 76 percent / VO(acac)2, TBHP / CH₂Cl₂ / 0.33 h / 20 °C

13: 90 percent / PPTS / methanol / 2 h / 20 °C

With 2,6-dimethylpyridine; hydrogenchloride; tert.-butylhydroperoxide; dichloro bis(acetonitrile) palladium(II); potassium osmate(VI); sodium periodate; lithium borohydride; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; bis(acetylacetonate)oxovanadium; N,N-dimethyl-ethanamine; dicyclohexylboron chloride; dihydrogen peroxide; iodine; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; pyridine hydrogenfluoride; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; zinc dibromide; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; tert-butyl alcohol;
DOI:10.1016/S0040-4039(96)02083-7

Reference yield:

: 93877-21-5
1,4-dibenzyloxybut-2-yne

: 185757-76-0
(2S,3R)-1,4-Bis-benzyloxy-2-((1R,4R,5R,6S)-6-benzyloxy-1-ethyl-5-hydroxy-2,7-dioxa-bicyclo[2.2.1]hept-4-yl)-butane-2,3-diol

Guidance literature:: Multi-step reaction with 14 steps

1: Bu₃SnH, Pd(PPh₃)4 / tetrahydrofuran

2: I₂ / CH₂Cl₂

3: 1.) n-BuLi, 2.) ZnBr₂, 3.) Pd(MeCN)2Cl₂ / 1.) THF, -78 deg C, 30 min, 2.) 2.5 h, 3.) DMF, from -78 deg C to 20 deg C, 2 h

4: 1M HCl / tetrahydrofuran / 4 h / 20 °C

5: 1.) (c-C₆H₁₁)2BCl, Et₃N, Me₂NEt, 3.) H₂O₂ / 1.) Et₂O, 0 deg C, 3 h, 2.) from -78 deg C to -18 deg C, 18 h, 3.) MeOH, pH 7 buffer

6: 76 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

7: 73 percent / LiBH₄ / tetrahydrofuran / 36 h / -78 - 20 °C

8: 82 percent / NaIO₄ / methanol / 1 h / 20 °C / pH 6.5 buffer

9: tetrahydrofuran / 2 h / -78 - 0 °C

10: TPAP, NMO / CH₂Cl₂ / 6 h / 20 °C

11: 88 percent / HF*py / pyridine; tetrahydrofuran

12: 61 percent / (DHQD)2PHAL, K₂OsO₄*2H₂O, NaHCO₃ / 2-methyl-propan-2-ol; H₂O / 14 h / 20 °C

13: 76 percent / VO(acac)2, TBHP / CH₂Cl₂ / 0.33 h / 20 °C

14: 90 percent / PPTS / methanol / 2 h / 20 °C

With 2,6-dimethylpyridine; hydrogenchloride; tert.-butylhydroperoxide; dichloro bis(acetonitrile) palladium(II); potassium osmate(VI); sodium periodate; lithium borohydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; bis(acetylacetonate)oxovanadium; N,N-dimethyl-ethanamine; dicyclohexylboron chloride; dihydrogen peroxide; iodine; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; pyridine hydrogenfluoride; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; zinc dibromide; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; tert-butyl alcohol;
DOI:10.1016/S0040-4039(96)02083-7