Methanesulfonic acid 2-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-ethyl ester

Base Information

Chemical Name:Methanesulfonic acid 2-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-ethyl ester
CAS No.:138629-16-0
Molecular Formula:C₂₃H₂₈O₇S
Molecular Weight:448.537
Hs Code.:

Synonyms:Methanesulfonic acid 2-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-ethyl ester

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of Methanesulfonic acid 2-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-ethyl ester

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Technology Process of Methanesulfonic acid 2-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-ethyl ester

There total 7 articles about Methanesulfonic acid 2-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-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: 98.0%

: 124-63-0
methanesulfonyl chloride

: 138629-15-9
2-((1S,2R,3S,4R,5R)-3,4-Bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-ethanol

: 138629-16-0
Methanesulfonic acid 2-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-ethyl ester

Guidance literature:: With triethylamine; In diethyl ether; at 0 ℃; for 3h;
DOI:10.1021/jo00028a017

Reference yield:

: 100-39-0
benzyl bromide

: 138629-16-0
Methanesulfonic acid 2-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 1) NaH, 2) imidazole / n-Bu₄NI / 1) THF, DMF, 0 deg C, 30 min., 2) r.t., 24 h

2: N-methylmorpholine N-oxide (NMMO), OsO₄ / acetone; H₂O / 6 h / Ambient temperature

3: NaIO₄ / methanol; H₂O / 2 h / Ambient temperature

4: NaBH₄ / methanol; diethyl ether / 1 h / 0 °C

5: 98 percent / Et₃N / diethyl ether / 3 h / 0 °C

With 1H-imidazole; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; sodium hydride; 4-methylmorpholine N-oxide; triethylamine; tetra-(n-butyl)ammonium iodide; In methanol; diethyl ether; water; acetone;
DOI:10.1021/jo00028a017

Reference yield:

: 74878-90-3
Toluene-4-sulfonic acid (1S,2S,3S,4R,5R)-2-allyl-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester

: 138629-16-0
Methanesulfonic acid 2-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: Na-Hg, methanol / 12 h / Ambient temperature

2: 1) NaH, 2) imidazole / n-Bu₄NI / 1) THF, DMF, 0 deg C, 30 min., 2) r.t., 24 h

3: N-methylmorpholine N-oxide (NMMO), OsO₄ / acetone; H₂O / 6 h / Ambient temperature

4: NaIO₄ / methanol; H₂O / 2 h / Ambient temperature

5: NaBH₄ / methanol; diethyl ether / 1 h / 0 °C

6: 98 percent / Et₃N / diethyl ether / 3 h / 0 °C

With 1H-imidazole; methanol; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; sodium amalgam; sodium hydride; 4-methylmorpholine N-oxide; triethylamine; tetra-(n-butyl)ammonium iodide; In methanol; diethyl ether; water; acetone;
DOI:10.1021/jo00028a017