(2R,3S,5S,6S)-3-Benzyloxy-6-methoxy-5-methyl-2-trityloxymethyl-tetrahydro-pyran

Base Information

Chemical Name:(2R,3S,5S,6S)-3-Benzyloxy-6-methoxy-5-methyl-2-trityloxymethyl-tetrahydro-pyran
CAS No.:145798-90-9
Molecular Formula:C₃₄H₃₆O₄
Molecular Weight:508.657
Hs Code.:

Synonyms:(2R,3S,5S,6S)-3-Benzyloxy-6-methoxy-5-methyl-2-trityloxymethyl-tetrahydro-pyran

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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 (2R,3S,5S,6S)-3-Benzyloxy-6-methoxy-5-methyl-2-trityloxymethyl-tetrahydro-pyran

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Technology Process of (2R,3S,5S,6S)-3-Benzyloxy-6-methoxy-5-methyl-2-trityloxymethyl-tetrahydro-pyran

There total 10 articles about (2R,3S,5S,6S)-3-Benzyloxy-6-methoxy-5-methyl-2-trityloxymethyl-tetrahydro-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:

: 100-39-0
benzyl bromide

: 68880-92-2
methyl 2,3-dideoxy-2-C-methyl-6-O-(triphenylmethyl)-α-D-arabino-hexopyranoside

: 145798-90-9
(2R,3S,5S,6S)-3-Benzyloxy-6-methoxy-5-methyl-2-trityloxymethyl-tetrahydro-pyran

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 1h;
DOI:10.1016/S0040-4039(00)79452-4

Reference yield:

: 118360-84-2
methyl 3,4-anhydro-2-deoxy-2-C-methyl-6-O-trityl-α-D-altropyranoside

: 145798-90-9
(2R,3S,5S,6S)-3-Benzyloxy-6-methoxy-5-methyl-2-trityloxymethyl-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 2 steps

1: 21 percent / LiBH₄ / tetrahydrofuran / 21 h / 25 °C

2: 1.) NaH / 1.) DMF, 0 deg C, 15 min, 2.) DMF, 0 deg C, 1 h

With lithium borohydride; sodium hydride; In tetrahydrofuran;
DOI:10.1246/bcsj.65.2974

Reference yield:

: 76-83-5
trityl chloride

: 145798-90-9
(2R,3S,5S,6S)-3-Benzyloxy-6-methoxy-5-methyl-2-trityloxymethyl-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 8 steps

1: 4-dimethylaminopyridine, pyridine / 24 h / 25 °C

2: 8 h / 25 °C

3: NaOMe / methanol; dioxane / 14 h / 25 °C

4: 80 percent / LiBr / dioxane / 72 h / 110 °C

5: 86 percent / CH₂Cl₂; diethyl ether / 0.75 h / Ambient temperature

6: 89 percent / NaH / dimethylformamide / 1 h / 0 °C

7: 21 percent / LiBH₄ / tetrahydrofuran / 21 h / 25 °C

8: 1.) NaH / 1.) DMF, 0 deg C, 15 min, 2.) DMF, 0 deg C, 1 h

With pyridine; dmap; lithium borohydride; sodium methylate; sodium hydride; lithium bromide; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1246/bcsj.65.2974