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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 46230Generated: October 27, 2026

2,3,4,6-Tetrakis-O-(phenylmethyl)-D-glucopyranose → (2-Chloro-4-methoxy-5-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)phenyl)methanol

https://huagongshe.com/reaction/46230

Reaction equation

Participants

RoleNameHCIDCharge
Reactant2,3,4,6-Tetrakis-O-(phenylmethyl)-D-glucopyranoseHCID 10940502—
Reactant(5-Bromo-2-chloro-4-methoxybenzyloxy)triisopropylsilaneHCID 53329406—
Product(2-Chloro-4-methoxy-5-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)phenyl)methanolHCID 53329585—

Reaction Steps

With similar method described in Step 3 of Example 92, (5-bromo-2-chloro-4-methoxybenzyloxy)triisopropylsilane (compound 89, 27.2 g, 66.7 mmol) and 2,3,4,6-tetra-O-benzyl-D-glucopyranose (compound 2, 30.0 g, 55.6 mmol) were converted to title compound (22.6 g, 59%, ca. 8:1 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-2c3a65c066ad4c4fa274a5b279ee8e5d
Source noteuspto-grants-2013_09