(2R,3S,4R,4aR,10bR)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-7-methyl-2,3,4,4a,5,10b-hexahydrothiochromeno[4,3-b]pyran

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Chemical Name:(2R,3S,4R,4aR,10bR)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-7-methyl-2,3,4,4a,5,10b-hexahydrothiochromeno[4,3-b]pyran
CAS No.:1426171-85-8
Molecular Formula:C₃₅H₃₆O₄S
Molecular Weight:552.734
Hs Code.:

Synonyms:(2R,3S,4R,4aR,10bR)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-7-methyl-2,3,4,4a,5,10b-hexahydrothiochromeno[4,3-b]pyran

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Chemical Property of (2R,3S,4R,4aR,10bR)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-7-methyl-2,3,4,4a,5,10b-hexahydrothiochromeno[4,3-b]pyran

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Technology Process of (2R,3S,4R,4aR,10bR)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-7-methyl-2,3,4,4a,5,10b-hexahydrothiochromeno[4,3-b]pyran

There total 2 articles about (2R,3S,4R,4aR,10bR)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-7-methyl-2,3,4,4a,5,10b-hexahydrothiochromeno[4,3-b]pyran 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: 94.0%

: 1426171-80-3
1-O-acetyl-3,4,6-tri-O-benzyl-2-deoxy-2-C-(2-methylphenyl)thiomethyl-α-D-mannopyranose

: 1426171-85-8
(2R,3S,4R,4aR,10bR)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-7-methyl-2,3,4,4a,5,10b-hexahydrothiochromeno[4,3-b]pyran

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 0.0833333h; diastereoselective reaction; Inert atmosphere; Molecular sieve;
DOI:10.1080/07328303.2012.762103

Reference yield:

: 162332-11-8
1,5-anhydro-2-deoxy-3,4,6-tri-O-benzyl-1,2-C-methylene-D-glycero-D-talo-hexitol

: 1426171-85-8
(2R,3S,4R,4aR,10bR)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-7-methyl-2,3,4,4a,5,10b-hexahydrothiochromeno[4,3-b]pyran

Guidance literature:: Multi-step reaction with 3 steps

1.1: N-iodo-succinimide / tetrahydrofuran; water / 12 h / 50 °C

1.2: 0.5 h / 20 °C

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 20 °C / Inert atmosphere

2.2: 0.08 h / 20 °C / Inert atmosphere

3.1: boron trifluoride diethyl etherate / dichloromethane / 0.08 h / 0 °C / Inert atmosphere; Molecular sieve

With N-iodo-succinimide; boron trifluoride diethyl etherate; sodium hydride; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; mineral oil; 3.1: |Friedel-Crafts Alkylation;
DOI:10.1080/07328303.2012.762103