((3aR,4R,6R,6aR)-6-Benzyloxymethyl-4-isothiocyanatomethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-methanol

Base Information

• Chemical Name: ((3aR,4R,6R,6aR)-6-Benzyloxymethyl-4-isothiocyanatomethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-methanol
• CAS No.: 364635-29-0
• Molecular Formula: C₁₈H₂₃NO₅S
• Molecular Weight: 365.45

Synonyms:((3aR,4R,6R,6aR)-6-Benzyloxymethyl-4-isothiocyanatomethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-methanol

Chemical Property of ((3aR,4R,6R,6aR)-6-Benzyloxymethyl-4-isothiocyanatomethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-methanol

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Technology Process of ((3aR,4R,6R,6aR)-6-Benzyloxymethyl-4-isothiocyanatomethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-methanol

There total 2 articles about ((3aR,4R,6R,6aR)-6-Benzyloxymethyl-4-isothiocyanatomethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-methanol 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:

thiophosgene (463-71-8) + 6-O-benzyl-2-deoxy-3,4-O-isopropylidene-2-aminomethyl-β-D-psicofuranose → ((3aR,4R,6R,6aR)-6-Benzyloxymethyl-4-isothiocyanatomethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-methanol (364635-29-0)

Guidance literature:

With water; calcium carbonate; In dichloromethane; at 20 ℃; for 6h;

DOI:10.1016/S0957-4166(01)00223-3

Reference yield:

6-O-benzyl-3,4-O-isopropylidene-β-D-psicofuranosyl cyanide (145121-55-7) → ((3aR,4R,6R,6aR)-6-Benzyloxymethyl-4-isothiocyanatomethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-methanol (364635-29-0)

Guidance literature:

Multi-step reaction with 2 steps

1: LiAlH₄ / diethyl ether / 0 - 20 °C

2: CaCO₃; H₂O / CH₂Cl₂ / 6 h / 20 °C

With lithium aluminium tetrahydride; water; calcium carbonate; In diethyl ether; dichloromethane;

DOI:10.1016/S0957-4166(01)00223-3

Reference yield: 85.0%

((3aR,4R,6R,6aR)-6-Benzyloxymethyl-4-isothiocyanatomethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-methanol (364635-29-0) → (2R,3R,4R,5R)-9-aza-2-benzyloxymethyl-3,4-dimethylmethylenedioxy-1,7-dioxaspiro[4.5]decane-8-thione

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 80 ℃; for 0.666667h;

DOI:10.1016/S0957-4166(01)00223-3

upstream raw materials:

thiophosgene

6-O-benzyl-3,4-O-isopropylidene-β-D-psicofuranosyl cyanide

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