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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 46224Generated: October 27, 2026

2,3,4,6-Tetrakis-O-(phenylmethyl)-D-glucopyranose → (3-((3S,4R,5R,6R)-3,4,5-Tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)naphthalen-1-yl)methanol

https://huagongshe.com/reaction/46224

Reaction equation

Participants

RoleNameHCIDCharge
Reactant2,3,4,6-Tetrakis-O-(phenylmethyl)-D-glucopyranoseHCID 10940502—
Reactant((3-Bromonaphthalen-1-yl)methoxy)triisopropylsilaneHCID 59463745—
Product(3-((3S,4R,5R,6R)-3,4,5-Tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)naphthalen-1-yl)methanolHCID 67287154—

Reaction Steps

With similar method described in Step 3 of Example 92, ((3-bromonaphthalen-1-yl)methoxy)triisopropylsilane (compound 76, 18.0 g, 45.6 mmol) and 2,3,4,6-tetra-O-benzyl-D-glucopyranose (2, 20.5 g, 38.0 mmol) were converted to title compound (23.3 g, 90%, ca. 2:1 mixture of anomers (13:0) as a white solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08541380B2
Source datasetuspto-grants-2013_09
ORD IDord-340547e3c1454fe5ae5d9e5a02207d7e
Source noteuspto-grants-2013_09